Dong Research Group


Click on any of the links below to see the list of publications in the corresponding year:
Publications in 2024



Xie, Qiqiang; Tugwell, Thomas; Li, Jiahao; Liu, Peng* and Dong, Guangbin* “Enantioconvergent carbenoid insertion into carbon−boron bonds” ChemRxiv. Preprint. [doi]



Choi, Shinyoung; Yoon, Ki-Young* and Dong, Guangbin* “Modular Synthetic Platform for Interior-Functionalized Dendritic Macromolecules Enabled by the Palladium/Norbornene Catalysis”  J. Am. Soc. Chem 2024. [doi]


Chen, Miao; Knox, Christian D.; Madhusudhanan, Mithun C.; Tugwell, Thomas T.; Liu, Coco; Liu, Peng* and Dong, Guangbin* “Stereospecific alkenylidene homologationof organoboronates by SNV reaction”  Nature 2024. [doi]


Liu, Xin; Zhu, Qi and Dong, Guangbin* “Beyond Tertiary Amines: Introducing Secondary Amines by Palladium/Norbornene-Catalyzed Ortho Amination”  Angew. Chem. Int. Ed. 2024 e202404042. [doi]


Choi, Shinyoung and Dong, Guangbin* “Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis”  J. Am. Chem. Soc. 2024, 146, 9512-9518. [doi]


Yu, Congjun; Zhang, Zining and Dong, Guangbin* “Split cross-coupling via Rh-catalysed activation of unstrained aryl-aryl bonds”  Nat. Catal. 2024, 7, 432-440. [doi]


Li, Gang; Wang, Hanfei; Loes, Michael; Saxena, Anshul; Yin, Jiangliang; Sarker, Mamun; Choi, Shinyoung; Aluru, Narayana*; Lyding, Joseph*; Sinitskii, Alexander* and Dong, Guangbin* “Hybrid Edge Results in Narrowed Band Gap: Bottom-up Liquid-phase Synthesis of Bent N=6/8 Armchair Graphene Nanoribbons”  ACS Nano 2024, 18, 4297-4307. [doi]


Chen, Miao; Tugwell, Thomas; Liu, Peng* and Dong, Guangbin* “Introducing Alkene Moieties via Iterative Carbenoid Insertions: Vinylene Homologation of Organoboronates” Nat. Synth. 2024, 3, 337-346. [doi]

190 Liu, Xin and Dong, Guangbin* “Asymmetric access to β-funebrene via a trans-selective annulation of allenylsilane-enes” Chem 2024, 10,1-2. [doi]

Rago, Alexander J.; Ye, Rong; Liu, Xin* and Dong, Guangbin* “A four-component reaction to access 3,3- disubstituted indolines via the palladium–norbornene-catalyzed ortho amination/ipso conjunctive coupling” Chem. Sci. 2024, 15, 1318-1323. [doi]

(invited contribution in commemoration of the 130th anniversary of Wuhan University.)

Publications in 2023



Xu, Yan* and Dong, Guangbin* “Deracemization through C–C bond manipulation” Sci. Bull. 2024, 69, 285-287 [doi]


Zhang, Rui; Yu, Tingting and Dong, Guangbin* “Rhodium catalyzed tunable amide homologation through a hook-and-slide strategy” Science 2023, 382, 951-957. [doi]

Highlighted by C&EN Synthesis, Synfacts, UChicago News, and “Some Items of Interest to Process R&D Chemists and Engineers


Lyu, Hairong; Tugwell, Thomas H.; Chen, Zhijie; Kukier, Garrett A.; Turlik, Aneta;Wu, Yifei; Houk, K. N.*; Liu, Peng* and Dong, Guangbin* “Modular synthesis of 1,2-azaborines via ring-opening BN-isostere benzannulation” Nat. Chem. 2024, 16, 269-276. [doi]

Highlighted by Synfacts.


Zhang, Zining; Zhu, Qi; Pyle, Daniel; Zhou, Xukai* and Dong, Guangbin* “Methyl Ketones as Alkyl Halide Surrogates: A Deacylative Halogenation Approach for Strategic Functional Group Conversions” J. Am. Chem. Soc. 2023, 145, 21096−21103. [doi]

Highlighted by “Some Items of Interest to Process R&D Chemists and Engineers

184 Liu, Xin; Zhou, Yun; Qi, Xiaotian; Li, Renhe*; Liu, Peng* and Dong, Guangbin* “Palladium/Norbornene-Catalyzed Direct Vicinal Di-Carbo-Functionalization of Indoles: Reaction Development and Mechanistic Study” Angew. Chem. Int. Ed. 2023. e202310697 [doi]

Liu, Xin; Fu, Yue.; Chen, Zhijie; Liu, Peng* and Dong, Guangbin* “Ortho-C–H Methoxylation of Aryl Halides Enabled by a Polarity Reversed N–O Reagent” Nat. Chem. 2023, 15, 1391-1399. [doi]

Highlighted by Synfacts and Nature Chemistry: News & Views


Yin, Jiangliang; Choi, Shinyoung; Pyle, Daniel; Guest, Jeffrey R. and Dong, Guangbin* “Backbone Engineering of Monodisperse Conjugated Polymers via Integrated Iterative Binomial Synthesis” J. Am, Chem. Soc. 2023, 145, 19120-19128. [doi]

Highlighted by Synfacts

181 Xie, Qiqiang; Zhang, Rui and Dong, Guangbin* “Programmable Amine Synthesis via Iterative Boron Homologation” Angew. Chem. Int. Ed. 2023, e202307118. [doi]
180 Huo, Jingfeng; Fu, Yue; Tang, Melody J.; Liu, Peng* and Dong, Guangbin* “Escape from Palladium: Nickel-Catalyzed Catellani Annulation” J. Am. Chem. Soc. 2023, 145, 11005-11011.[doi]
179 Xie, Jiaxin and Dong, Guangbin* “Cyclopropylcarbinyl cation chemistry in synthetic method development and natural product synthesis: cyclopropane formation and skeletal rearrangement” Org. Chem. Front. 2023, 10, 2346–2358. [doi]
178 Xue, Yibin; Parsad, Arjuna and Dong, Guangbin* “α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis” Org. Synth. 2023, 100, 99-112.[doi]
177 Zhou, Xukai; Pyle, Daniel; Zhang, Zining and Dong, Guangbin* “Deacylative Thiolation by Redox-Neutral Aromatization-Driven C−C Fragmentation of Ketones” Angew. Chem., Int. Ed. 2023, 62, e202213691. [doi]
176 Xie, Jiaxin; Zheng, Zhong; Liu, Xin; Zhang, Nan; Choi, Shinyoung; He, Chuan and Dong, Guangbin* Asymmetric Total Synthesis of (+)-Phainanoid A and Biological Evaluation of the Natural Product and Its Synthetic Analogues” J. Am. Chem. Soc. 2023, 145, 4828–4852. [doi]
Publications in 2022



Zhou, Bo; Deng, Shuang.; Xu, Yin.; Qi, Xiaotian and Dong, Guangbin* Iridium-Catalyzed Intramolecular β-C–H Alkenylation of Ketones with Alkynes via a Hydride-Transfer Approach” J. Am. Chem. Soc. 2022, 144, 23230–23238. [doi]


Hou, Si-Hua; Yu, Xuan; Zhang, Rui; Wagner, Cole and and Dong, Guangbin* “Rhodium-Catalyzed Diastereo- and Enantioselective Divergent Annulations between Cyclobutanones and 1,5-Enynes: Repaid Construction of Complex C(sp3)-Rich Scaffolds” J. Am. Chem. Soc. 2022, 144, 22159–22169. [doi]

* Highlighted by Organic Process Research & Development and Synfacts


Yang, Sen; Fan, Huike; Xie, Licheng; Dong, Guangbin* and Chen, Ming* “Photoinduced Desaturation of Amides by Palladium Catalysis” Org. Lett.. 2022, 24, 6460–6465. [doi]


Yin, Jiangliang; Jacobse, Peter H.; Pyle,Daniel; Wang, Ziyi; Crommie, Michael F.* and Dong, Guangbin* “Programmable Fabrication of Monodisperse Graphene Nanoribbons via Deterministic Iterative Synthesis” J. Am. Chem. Soc. 2022, 144, 16012–16019. [doi]


Xue, Yibin and Dong, Guangbin* “Deconstructive Synthesis of Bridged and Fused Rings via Transition-Metal-Catalyzed “Cut-and-Sew” Reactions of Benzocyclobutenones and Cyclobutanones” Acc. Chem. Res. 2022, 55, 2341–2354. [doi]


Zhou, Xukai; Yu, Tingting and Dong, Guangbin* “Site-Specific and Degree-Controlled Alkyl Deuteration via Cu-Catalyzed Redox-Neutral Deacylation” J. Am. Chem. Soc. 2022, 144, 9570–9575. [doi]


Yu, Xuan; Zhang, Zining and Dong, Guangbin* “Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C–C Activation and Sulfonyl Radical Migration” J. Am. Chem. Soc. 2022, 144, 9222–9228. [doi]


Xie, Qiqiang and Dong, Guangbin* “Programmable Ether Synthesis Enabled by Oxa-Matteson Reaction” J. Am. Chem. Soc. 2022, 144, 8498–8503. [doi]


Huang, Jiangkun; Zhang, Rui; Wu, Xiuli; Dong, Guangbin* and Xia, Ying* “Intramolecular One-Carbon Homologation of Unstrained Ketones via C–C Activation-Enabled 1,1-Insertion of Alkenes” Org. Lett. 2022, 24, 2436–2440. [doi]


Ochi, Shusuke; Zhang, Zining; Xia, Ying* and Dong, Guangbin* “Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes” Angew. Chem., int. Ed. 2022, 61, e202202703. [doi]

* Highlighted by Synfacts



Wu, Zhao and Dong, Guangbin* “Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis” Angew. Chem., Int. Ed. 2022, 61, e202201239. [doi]



Zhu, Jun; Xue, Yibin; Zhang, Rui; Ratchford, Benjamin L. and Dong, Guangbin* “Catalytic Activation of Unstrained C(Aryl)–C(Alkyl) Bonds in 2,2′-Methylenediphenols” J. Am. Chem. Soc. 2022, 144, 3242–3249. [doi]



Publications in 2021



Zhou, Xukai; Xu, Yan* and Dong, Guangbin* “Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones” J. Am. Chem. Soc. 2021, 143, 20042–20048. [doi]



Xie, Jiaxin; Liu, Xin; Zhang, Nan; Choi, Shinyoung and Dong, Guangbin* “Bidirectional Total Synthesis of Phainanoid A via Strategic Use of Ketones” J. Am. Chem. Soc. 2021, 143, 19311-19316. [doi]

* Highlighted by Organic Chemistry Portal and Synfacts


Wu, Zhao; Xu, Xiaolong; Wang, Jianchun and Dong, Guangbin* “Carbonyl 1,2-transposition through triflate-mediated α-amination” Science 2021, 374, 734-740. [doi]

* Highlighted by C&EN, UChicago News, Synform and Synfacts


Ashfeld, Brandon L.; Judd, Andrew S.; Xie, Jiaxin and Dong, Guangbin “Chloro(1,5-Cyclooctadiene)Rhodium(I) Dimer” Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd: Hoboken, NJ, 2021. [doi]



Li, Renhe and Dong, Guangbin* “Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles” Angew. Chem., Int. Ed. 2021, 60, 26184-26191. [doi]

* Highlighted by Synfacts


Xie, Qiqiang and Dong, Guangbin* “Aza-Matteson Reactions via Controlled Mono- and Double-Methylene Insertions into Nitrogen–Boron Bonds” J. Am. Chem. Soc. 2021, 143, 14422-14427. [doi]



Zhou, Xukai.; Xu, Yan* and Dong, Guangbin* “Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones” Nat. Catal. 2021, 4, 703-710. [doi]


Zhu, Jun‡.; Zhang, Rui‡ and Dong, Guangbin* “Orthogonal cross-coupling through intermolecular metathesis of unstrained C(aryl)–C(aryl) single bonds” Nat. Chem. 2021, 13, 836-842. [doi]

* Highlighted by C&EN



Zhou, Bo.; Qi, Xiaotian.;* Liu, Peng.* and Dong, Guangbin* “Development and Mechanistic Studies of the Iridium-catalyzed C−H Alkenylation of Enamides with Vinyl Acetates: A Versatile Approach for Ketone Functionalization” Angew. Chem., Int. Ed. 2021, 60, 20926-20934. [doi]


Zhang, Rui; Xia, Ying and Dong, Guangbin* “Intermolecular [5+2] Annulation between 1-Indanones and Internal Alkynes by Rh-catalyzed C−C Activation” Angew. Chem., Int. Ed. 2021, 60, 20476-20482. [doi]



Liu, Xin; Wang, Jianchun* and Dong, Guangbin* “Modular Entry to Functionalized Tetrahydrobenzo[b]azepines via the Palladium/Norbornene Cooperative Catalysis Enabled by a C7-Modified Norbornene” J. Am. Chem. Soc. 2021, 143, 9991–10004. [doi]



Xue, Yibin and Dong, Guangbin* “Total Synthesis of Penicibilaenes via C–C Activation-Enabled Skeleton Deconstruction and Desaturation Relay-Mediated C–H Functionalization” J. Am. Chem. Soc. 2021, 143, 8272-8277. [doi]


Wu, Zhao; Fatuzzo, Nina and Dong, Guangbin* “Palladium/Norbornene-Catalyzed Distal Alkenyl C–H Arylation and Alkylation of cis-Olefins” Tetrahedron 2021, 90, 132173. [doi]

* Special issue in honor of Prof. Stephen Martin for his immense service to Tetrahedron, his Award and to the Tetrahedron Symposium and to our field in general.


Tsogoeva, Svetlana B*; Dong, Guangbin* and Ackermann, Lutz* “Editorial: The Catalysis of Ring Synthesis” ChemCatChem 2021, 13, 1–4. [doi]


Rago, Alexander J. and Dong, Guangbin* “Synthesis of C3,C4-Disubstituted Indoles via the Palladium/Norbornene-Catalyzed ortho-Amination/ipso-Heck Cyclization” Org. Lett. 2021, 23, 3755-3760. [doi]


Hairong Lyu; Kevlishvili, Ilia; Yu, Xuan; Liu, Peng* and Dong, Guangbin* “Boron insertion into alkyl ether bonds via zinc/nickel tandem catalysis” Science 2021, 372, 175-182. [doi]


Zhang, Rui and Dong, Guangbin* “Transfer hydroarylation of ketones using directing-group-free, unstrained alcohols” Chem 2021, 7, 841-842. [doi]


“Deconstructive Asymmetric Total Synthesis of Morphine‐Family Alkaloid (‐)‐Thebainone A” Hou, Si-Hua; Prichina, Adriana Y. and Dong, Guangbin* Angew. Chem. Int. Ed. 2021, 60, 13057-13064. [doi]


Rago, Alexander J. and Dong, Guangbin* “Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C–H activation” Green Synth. Catal. 2021, 2, 216-227. [doi]


Chen, Ming and Dong, Guangbin* “Platinum‐catalyzed α,β‐Desaturation of Cyclic Ketones through Direct Metal‐enolate Formation” Angew. Chem. Int. Ed. 2021, 60, 7956-7961. [doi]

Publications in 2020


Yoon, Ki-Young and Dong, Guangbin* “Multicomponent Polymerization for π‐Conjugated Polymersa” Macromol. Rapid Commun. 2020, 2000646. [doi]


Chen, Xiao-Yang; Zhou, Xukai; Wang, Jianchun and Dong, Guangbin* “FMPhos: Expanding the Catalytic Capacity of Small-Bite-Angle Bisphosphine Ligands in Regioselective Alkene Hydrofunctionalizations” ACS Catal. 2020, 10, 14349-14358. [doi]


Li, Renhe and Dong, Guangbin* “Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis” J. Am. Chem. Soc. 2020,142, 17859-17875. [doi]


Qi, Xiaotian; Wang, Jianchun; Dong, Zhe; Dong, Guangbin* and Liu, Peng* “Compatibility Score for Rational Electrophile Selection in Pd/NBE Cooperative Catalysis” Chem. 2020, 6, 2810-2825. [doi]


Xia, Ying* and Dong, Guangbin* “Temporary or removable directing groups enable activation of unstrained C–C bonds” Nat. Rev. Chem. 2020, 4, 600-614.  [doi]


Hou, Si-Hua; Yu, Xuan; Zhang, Rui; Deng, Lin; Zhang, Mengxi; Prichina, Adriana Y and Dong, Guangbin* “Enantioselective Type II Cycloaddition of Alkynes via C−C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles” J. Am. Chem. Soc. 2020, 142, 13180-13189. [doi]


Ochi, Shusuke; Xia, Ying* and Dong, Guangbin* “Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C−C Activation of Cyclopentanones” Bull. Chem. Soc. Jpn. 2020, 93, 1213-1217. [doi]

* Special issue on “Frontiers of Molecular Science”

* Selected as “Selected Paper in the issue


Tsukamoto, Tatsuhiro* and Dong, Guangbin* “Catalytic Dehydrogenative Cyclization of o-Teraryls under pH-Neutral and Oxidant-Free Conditions” Angew. Chem. Int. Ed. 2020, 59, 15249-15253. [doi]


Wang, Chengpeng and Dong, Guangbin* “Catalytic β-Functionalization of Carbonyl Compounds Enabled by α,β-Desaturation” ACS Catal. 2020, 10, 6058–6070. [doi]


Wang, Chengpeng; Naren, Nevin A.; Zheng, Pengfei* and Dong, Guangbin* “Intramolecular β-Alkenylation of Cyclohexanones via Pd-Catalyzed Desaturation-Mediated C(sp3)–H/Alkyne Coupling” J. Am. Chem. Soc. 2020, 142, 8962–8971. [doi]

* Highlighted by SYNFACTS


Rago, Alexander J. and Dong, Guangbin* “Unexpected ortho-Heck Reaction under the Catellani Conditions” Org. Lett. 2020, 22, 3770–3774. [doi]


Chen, Tiantian; Yang, Haijian; Yang, Yang; Dong, Guangbin* and Xing, Dong* “Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions” ACS Catalysis 2020, 10, 4238–4243. [doi]


Hou, Si-Hua; Prichina, Adriana Y; Zhang, Mengxi and Dong, Guangbin* “Asymmetric Total Syntheses of Di- and Sesqui-Terpenoids via Catalytic C–C Activation of Cyclopentanones” Angew. Chem. Int. Ed. 2020, 59, 7848–7856. [doi]

* Highlighted by Organic Chemistry Portal


Wu, Zhao; Fatuzzo, Nina and Dong, Guangbin* “Distal Alkenyl C–H Functionalization via the Palladium/Norbornene Cooperative Catalysis” J. Am. Chem. Soc. 2020, 142, 2715-2720. [doi]


Wang, Jianchun; Zhou, Yun; Xu, Xiaolong; Liu, Peng and Dong, Guangbin* “Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the “Meta Constraint” in the Palladium/Norbornene Catalysis” J. Am. Chem. Soc. 2020, 142, 3050-3059. [doi]


Xu, Yan and Dong, Guangbin* “Deconstructive ketone functionalization: A new application of LMCT-promoted C–C cleavage” Chem 2020, 6, 10-11. [doi]


Deng, Lin and Dong, Guangbin* “Carbon‒Carbon Bond Activation of Ketones” Trends in Chemistry 2020, 2, 183-198. [doi]

Publications in 2019



Li, Renhe; Zhou, Yun; Xu, Xiaolong and Dong, Guangbin* “Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis” J. Am. Chem. Soc. 2019, 141, 18958-18963 [doi]

* Highlighted by JACS spotlight


Wang, Jianchun; Dong, Zhe; Yang, Cheng and Dong, Guangbin* “Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction” Nat. Chem. 2019, 11, 1106-1112. [doi]

* Highlighted by Nature Chemistry, UChicago News, Synfact and Chem-Station.


Zhu, Jun; Chen, Peng-hao; Lu, Gang; Liu, Peng* and Dong, Guangbin* “Ruthenium-Catalyzed Reductive Cleavage of Unstrained Aryl─Aryl Bonds: Reaction Development and Mechanistic Study” J. Am. Chem. Soc. 2019, 141, 18630-18640. [doi]


Yoon, Ki-Young and Dong, Guangbin* “Liquid-phase bottom-up synthesis of graphene nanoribbons” Mater. Chem. Front. 2020, 4, 29-45. [doi]


Deng, Lin; Fu, Yue; Lee, Siu Yin; Wang, Chengpeng; Liu, Peng* and Dong, Guangbin* “Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature” J. Am. Chem. Soc. 2019, 141, 16260-16265. [doi]


Chen, Ming and Dong Guangbin* “Copper-Catalyzed Desaturation of Lactones, Lactams and Ketones under pH-Neutral Conditions” J. Am. Chem. Soc. 2019, 141, 14889−14897. [doi]


Xia, Ying; Ochi, Shusuke; and Dong, Guangbin* “Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon-Carbon Bonds” J. Am. Chem. Soc. 2019, 141, 13038−13042. [doi]



Li, Renhe; Zhou, Yun; Yoon, Ki-Young; Dong, Zhe; and Dong, Guangbin* “Sulfenamide-enabled Ortho Thiolation of Aryl Iodides via Palladium/Norbornene Cooperative Catalysis” Nature Communications 2019, 10, 3555. [doi]


Zheng, Pengfei; Wang, Chengpeng; Chen, Ying-Chun; and Dong, Guangbin* “Pd-Catalyzed Intramolecular α‑Allylic Alkylation of Ketones with Alkynes: Rapid and Stereodivergent Construction of [3.2.1] Bicycles” ACS Catal. 20199, 5515-5521. [doi]


Wang, Jianchun; and Dong, Guangbin* “Palladium/Norbornene Cooperative Catalysis” Chem. Rev. 2019119, 7478-7528 [doi]


Wang, Chengpeng; Rago, Alexander J.; and Dong, Guangbin* “Direct β-Alkenylation of Ketones via Pd-Catalyzed Redox Cascade” Org. Lett. 2019, 9, 3377-3381. [doi]


Li, Renhe; Liu, Feipeng; and Dong, Guangbin* “Redox-Neutral ortho Functionalization of Aryl Boroxines via Palladium/Norbornene Cooperative Catalysis” Chem 2019, 5, 929-939. [doi]


Yoon, Ki-Young; Xue, Yazhen; and Dong, Guangbin* “Three-Step Synthesis of a Less-Aggregated Water-Soluble Poly(p-phenylene ethynylene) with Meta Side Chains via Palladium/Norbornene Cooperative Catalysis” Macromolecules 201952, 1663-1670. [doi]


Xu, Yan; Qi, Xiaotian; Zheng, Pengfei; Berti, Carlo C.; Liu, Peng;* and Dong, Guangbin* “Deacylative transformations of ketones via aromatization-promoted C–C bond activation” Nature 2019567, 373-378. [doi]

* Highlighted by UChicago.

* Highlighted by SYNFACTS


Xing, Dong; Qi, Xiaotian; Marchant, Daniel; Liu, Peng,* and Dong, Guangbin* “Branched-Selective  Direct  a-Alkylation  of  Cyclic  Ketones  with  Simple Alkenes”  Angew. Chem. Int. Ed. 2019, 58, 4366-4370. [doi]


Hot paper
Liu, Feipeng; Dong, Zhe; Wang, Jianchun*; and Dong, Guangbin* “Palladium/Norbornene‐Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A” Angew. Chem. Int. Ed. 201958, 2144-2148. [doi]


Zhu, Jun; Wang, Jianchun; and Dong, Guangbin* “Catalytic activation of unstrained C(aryl)–C(aryl) bonds in 2,2′-biphenols” Nat. Chem. 201911, 45-51. [doi]

* Highlighted by UChicago News.

* Highlighted by SYNFACTS


Lim, Hee Nam; Xing, Dong; and Dong, Guangbin* “Transition-Metal-Catalyzed Ketone α-Alkylation and Alkenylation with Simple Alkenes and Alkynes through a Dual Activation Strategy” Synlett 2019, 30, 674-684. [doi]

* Invited contribution

Publications in 2018



Chen, Tiantian; Yang, Yang; Xie, Liyu; Yang, Haijian; Dong, Guangbin*; and Xing, Dong* “Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions” ChemRxiv. Preprint. [doi]



Chen, Ming; Rago, Alexander; and Dong, Guangbin* “Platinum‐catalyzed Desaturation of Lactams, Ketones and Lactones” Angew. Chem. Int. Ed. 201857, 16205-16209. [doi]

*Highlighted by SYNFACTS


Li, Renhe; Liu, Feipeng; and Dong, Guangbin* “Palladium-Catalyzed Asymmetric Annulation Between Aryl Iodides and Racemic Epoxides Using a Chiral Norbornene Cocatalyst” Org. Chem. Front. 20185, 3108-3112. [doi]

106 Jin, Likun ‡ ; Wang, Jianchun ‡ ; and Dong, Guangbin* “Palladium‐Catalyzed γ‐C(sp3)‐H Arylation of Thiols via a Detachable Protecting/Directing Group” Angew. Chem. Int. Ed. 201857, 12352-12355. [doi]

Deng, Lin; Chen, Mengqing; and Dong, Guangbin* “Concise Synthesis of (-)-Cycloclavine and (-)-5-epi-Cycloclavine via Asymmetric C-C Activation” J. Am. Chem. Soc. 2018120, 9652-9658. [doi]

*Highlighted by SYNFACTS


Wang, Jianchun; Li, Renhe; Dong, Zhe; Liu, Peng; and Dong, Guangbin* “Complementary site-selectivity in arene functionalization enabled by overcoming the ortho constraint in palladium/norbornene catalysis” Nat. Chem. 201810, 866-872. [doi]

*Highlighted by Chemical & Engineering News, vol 96, issue 27, Jul 1, 2018.

Reversing rules of arene chemistry. Electronics reign in the realm of electrophilic aromatic substitutions.  Reactions using a palladium catalyst combined with a norbornene cofactor offer reversed site selectivity in aryl iodides, but they come with caveats. Guangbin Dong’s lab at the University of Chicago has developed a novel norbornene compound that lifts one of those limitations. In one example, the researchers accomplished a late-stage amination of the pesticide strychnine that had previously taken seven steps in only two steps.

*Highlighted by UChicago News.

*Highlighted by Chem, 20184, 1775-1777.

103 Dong, Zhe; Lu, Gang; Wang, Jianchun; Liu, Peng; and Dong, Guangbin* “Modular ipso/ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis” J. Am. Chem. Soc. 2018140, 8551-8562. [doi]
102 Yoon, Ki-Young and Dong, Guangbin* “Modular in situ‐Functionalization Strategy: Multicomponent Polymerization by Palladium/Norbornene Cooperative Catalysis” Angew. Chem. Int. Ed. 201857, 8592-8596. [doi]
101 Wang, Chengpeng and Dong, Guangbin* “Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade” J. Am. Chem. Soc. 2018140, 6057–6061. [doi]

Li, Gang; Yoon, Ki-Young; Zhong, Xinjue; Wang, Jianchun; Zhang, Rui; Guest, Jeffrey R.; Wen, Jianguo; Zhu, X.-Y.; and Dong, Guangbin* “A modular synthetic approach for band-gapengineering of armchair graphene nanoribbons” Nat. Commun. 20189, 1687.  [doi]


Xia, Ying; Wang, Jianchun; and Dong, Guangbin* “Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds” J. Am. Chem. Soc. 2018140, 5347-5351.  [doi]

*Highlighted by Nature Catalysis

*Highlighted by Chem


Pan, Saiyong; Chen, Sicong; and Dong, Guangbin* “Divergent Total Syntheses of Enmein-Type Natural Products: (–)-Enmein, (–)-Isodocarpin and (–)-Sculponin R” Angew. Chem. Int. Ed. 201857, 6333-6336.  [doi]


Huang, Zhongxing; and Dong, Guangbin* “Palladium-catalyzed redox cascade for direct β-arylation of ketones” Tetrahedron 201874, 3253-3265.  [doi]


Sun, Tianwen; Zhang, Yuna; Qiu, Bo; Wang, Yafei; Qin, Yuting; Dong, Guangbin*; and Xu, Tao.* “Rhodium(I)-Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones” Angew. Chem. Int. Ed. 201857, 2859-2863.  [doi]


Chen, Ming; Liu, Feipeng; and Dong, Guangbin.* “Direct Palladium-Catalyzed β-Arylation of Lactams” Angew. Chem. Int. Ed. 201857, 3815-3819.  [doi]


Xu, Yan; and Dong, Guangbin.* “sp3 C–H activation via exo-type directing groups” Chem. Sci. 20189, 1424-1432.  [doi]


Deng, Lin; Jin, Likun; and Dong, Guangbin.* “Fused-Ring Formation via an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes” Angew. Chem. Int. Ed. 201857, 2702-2706. [doi]


Zhu, Zixi; Li, Xinghan; Chen, Sicong; Chen, Peng-hao; Billett, Brent A.; Huang, Zhongxing; and Dong, Guangbin.* “Cobalt-Catalyzed Intramolecular Alkyne/Benzocyclobutenone Coupling: C–C Bond Cleavage via a Tetrahedral Dicobalt Intermediate” ACS Catal. 20188, 845-849.  [doi]


Li, Renhe and Dong, Guangbin.* “Direct Annulation between Aryl Iodides and Epoxides via Palladium/Norbornene Cooperative Catalysis” Angew. Chem. Int. Ed201857, 1697-1701.  [doi]

*Hightlighted by Synfacts


Thompson, Samuel J.; Brennan, Marshall R.; Lee, Siu Yin and Dong, Guangbin.* “Synthesis and applications of rhodium porphyrin complexes” Chem. Soc. Rev. 201847, 929-981  [doi]


Rong, Zi-Qiang, Lim, Hee Nam; and Dong, Guangbin.* “Intramolecular Acetyl Transfer to Olefins via Catalytic C-C Bond Activation of Unstrained Ketones” Angew. Chem. Int. Ed201857, 475-479. [doi]

Publications in 2017


Xing, Dong and Dong, Guangbin.* “Branched-Selective Intermolecular Ketone α-Alkylation with Unactivated Alkenes via an Enamide Directing Strategy” J. Am. Chem. Soc. 2017, 139, 13664-13667. [doi]


Chen, Ming and Dong, Guangbin.* “Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization” J. Am. Chem. Soc. 2017139, 7757–7760.  [doi]

*Highlighted by Org. Process Res. Dev. 201721, 1873.


Xie, Jiaxin; Wang, Jianchun; and Dong, Guangbin.* “Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation” Org. Lett. 201719, 3017-3020. [doi]


Xu, Yan; Young, Michael C.; and Dong, Guangbin.* “Catalytic Coupling between Unactivated Aliphatic C–H Bonds and Alkynes via a Metal–Hydride Pathway” J. Am. Chem. Soc. 2017, 139, 5716-5719. [doi]

*Highlighted by Organic Chemistry Portal. [link]


Huang, Zhongxing; and Dong, Guangbin.* “Site-Selectivity Control in Organic Reactions: A Quest To Differentiate Reactivity among the Same Kind of Functional Groups” Acc. Chem. Res. 201750, 465−471. [doi]


Zhang, Hang‡; Wu, Guojiao ‡; Yi, Heng; Sun, Tong; Wang, Bo; Zhang, Yan; Dong, Guangbin; Wang, Jianbo.* “Copper(I)-Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring-Opening C-C Bond Formations” Angew. Chem. Int. Ed. 201756, 3945-3950. [doi]


Dong, Zhe; Ren, Zhi; Thompson, Samuel; Xu, Yan; Dong, Guangbin* “Transition-Metal-Catalyzed C−H Alkylation Using Alkenes” Chem. Rev. 2017117, 9333. [doi]


Xia, Ying; Wang, Jianbo; and Dong, Guangbin.* “Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones” Angew. Chem. Int. Ed. 201756, 2376-2380. [doi]


Chen, Peng-hao; Billett, Brent; Tsukamoto, Tatsuhiro; Dong, Guangbin.* ““Cut and Sew” Transformations via Transition-Metal-Catalyzed Carbon–Carbon Bond Activation” ACS Catal20177, 1340-1360. [doi]


Publications in 2016


Zhou, Xuan; and Dong, Guangbin.* “Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles” Angew. Chem. Int. Ed. 201655, 15091. [doi]


Xia, Ying; Lu, Gang; Liu, Peng; and Dong, Guangbin.* “Catalytic Activation of Carbon–carbon Bonds in Cyclopentanones” Nature, 2016539, 546 [doi]

*Highlighted by Chemical & Engineering News94(44), Nov 7, 2016.

Breaking bonds in unstrained rings Catalyst system activates carbon-carbon bonds in cyclopentanones. “This incredible transformation makes an elegant addition to the synthetic toolbox,” comments Masahiro Murakami, an expert in organic chemistry at Kyoto University. “Carbon-carbon and carbon-hydrogen bonds are robust sigma bonds,” he notes. In this new reaction such bonds “are not only both broken but also swapped, making a totally different framework,” he says.


Wang, Jianchun;‡ Zhang, Lei;‡ Dong, Zhe;* and Dong, Guangbin.* “Reagent-Enabled ortho-Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis” Chem 2016, 1, 581. [doi]

*Highlighted by Chem 2016, 1, 522.

*Chosen as the cover for Chem, Vol 1, Issue 4.



Zhou, Xuan; Ko, Haye Min;* and Guangbin Dong.* “Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins” Angew. Chem. Int. Ed. 201655, 13867.  [doi]


Chen, Peng-hao and Dong, Guangbin.* “Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis” Chem. Eur. J. 201622, 18290. [doi]


Hot Paper
Xu, Yan‡; Young, Michael‡; Wang, Chengpeng; Magness, David ; and Guangbin Dong.* “Catalytic C(sp3 )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ.” Angew. Chem., Int. Ed.201655, 9084. [doi]


Li, Gang; Yoon, Ki-young; Zhong, Xinjue; Zhu, Xiao-Yang;* Dong, Guangbin.* “Efficient Bottom-Up Preparation of Graphene Nanoribbons via Mild Suzuki-Miyaura Polymerization of Simple Triaryl Monomers.” Chem. Eur. J.201622, 9116. [doi]


Hayes, Colin; Chen, Peng-hao; Thedford, Paxton; Ellison, Christopher; Dong, Guangbin; Willson, Grant.* “Effect of Ring Functionalization on the Reaction Temperature of Benzocyclobutene Thermoset Polymers.” Marcomolecules,  201649 , 3706. [doi]


Ren, Zhi; Dong, Guangbin.* “Direct Observation of C−H Cyclopalladation at Tertiary Positions Enabled by an Exo-Directing Group”. Organometallics2016, 35, 1057. [doi]


Huang, Zhongxing; Wang, Chengpeng; Dong, Guangbin.* “A Hydrazone-Based exo-Directing Group Strategy for β-C–H Oxidation of Aliphatic Amines”. Angew. Chem., Int. Ed. 201655, 5299. [doi]

*Highlighted by the Organic Chemistry Portal! [link]


Lim, Hee Nam; Dong, Guangbin.* “Catalytic Cage Formation via Controlled Dimerization of Norbornadienes: An Entry to Functionalized HCTDs (Heptacyclo[,6.03,13.04,11.05,9.010,14]tetradecanes)”. Org. Lett. 2016,18, 1104. [doi]


Xu, Yan; Su, Tianshun; Huang, Zhongxing; Dong, Guangbin.* “Practical Direct α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis”. Angew. Chem., Int. Ed. 201655, 2559. [doi]


Zeng, Rong; Chen, Peng-hao; Dong, Guangbin.* “Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates”. ACS Catal. 20166, 969-973. [doi]


Deng, Lin; Xu, Tao; Li, Hongbo; Dong, Guangbin.* “Enantioselective Rh-catalyzed Carboacylation of C=N Bonds via C−C Activation of Benzocyclobutenones”. J. Am. Chem. Soc. 2016138, 369-374. [doi]

*Highlighted by Synfacts 2016; 12(3): 0288.


Invited Review:
Whittaker, R. E.; Dermenci, Alpay; Dong, Guangbin.* “Synthesis of Ynones and Recent Application in Transition-Metal-Catalyzed Reaction”. Synthesis 201648, 161. [doi]


Publications in 2015


Mo, Fanyang; Lim, Hee Nam; Dong, Guangbin.* “Bi-functional Ligand-assisted Catalytic Ketone α-Alkenylation with Internal Alkynes: Controlled Synthesis of Enones and Mechanistic Studies”. J. Am. Chem. Soc. 2015137, 15518-15527.[doi]


Whittaker, R. E.; Dong, Guangbin.* “Controlled Rh-Catalyzed Mono- and Double-decarbonylation of Alkynyl α-Diones to Form Conjugated Ynones and Disubstituted Alkynes”. Org. Lett. 201517, 5504-5507. [doi]


Lim, Hee Nam; Dong, Guangbin.* “Catalytic Intramolecular Ketone Alkylation with Olefins by Dual Activation”. Angew. Chem., Int. Ed. 201554, 15294-15298. [doi]


Zhou, Xuan; Dong, Guangbin.* “(4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C−C Activation”. J. Am. Chem. Soc. 2015137, 13715-13721. [doi]

*Highlighted by Synfacts 2016; 12(1): 0041.


Dong, Zhe; Wang, Jianchun; Ren, Zhi; Dong, Guangbin.* “Ortho C−H Acylation of Aryl Iodides by Palladium/Norbornene Catalysis”. Angew. Chem., Int. Ed. 201554, 12664-12668. [doi]


Thompson, Samuel J.; Thach, Danny Q.; Dong, Guangbin.* “Cyclic Ether Synthesis via Palladium-Catalyzed Directed De-hydrogenative Annulation at Unactivated Terminal Positions”. J. Am. Chem. Soc. 2015137, 11586-11589. [doi]


Xu, Yan; Yan, Guobing; Ren, Zhi; Dong, Guangbin.* “Diverse sp3 C−H Functionalization Through Alcohol β-Sulfonyloxylation”. Nat. Chem. 20157, 829-834. [doi]

*Highlighted by the Japanese Language Chem-Station! [link]
*2nd Most Read Paper in Previous 15 Days (September 7th, 2015)! [link]


Huang, Zhongxing; Sam, Quynh P.; Dong, Guangbin.* “Palladium-Catalyzed Direct β-Arylation of Ketones with Diaryliodonium Salts: a Stoichiometric Heavy Metal-Free and User-Friendly Approach”. Chem. Sci. 20156, 5491-5498. [doi]


Huang, Zhongxing; Lim, Hee Nam; Mo, Fanyang; Young, Michael C.; Dong, Guangbin.* “Transition Metal-Catalyzed Ketone-Directed or Mediated C−H Functionalization”. Chem. Soc. Rev. 201544, 7764. [doi]


Chen, Peng-hao; Sieber, Joshua; Senanyake, Chris. H.; Dong, Guangbin.* “Rh-Catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones”. Chem. Sci. 20156, 5440-5445. [doi]


Lu, Gang; Fang, Cheng, Xu, Tao; Dong, Guangbin; Liu, Peng.* “Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones”. J. Am. Chem. Soc. 2015137, 8274-8283. [doi]


Ren, Zhi; Schulz, Jonathan E.; Dong, Guangbin.* “Catalytic Ortho-Acetoxylation of Masked Benzyl Alcohols via an Exo-Directing Mode”. Org. Lett. 201517, 2696-2699. [doi]


Zhe, Dong; Wang, Jianchun; Dong, Guangbin.* “Simple Amine-Directed meta-Selective C−H Arylation via Pd/Norbornene Catalysis”. J. Am. Chem. Soc. 2015137, 5887-5890. [doi]

*Highlighted by the Organic Chemistry Portal! [link]
*Highlighted by JOC 2016; 81(2): 343.


Dermenci, Alpay; Whittaker, Rachel E.; Gao, Yang; Cruz, Faben; Yu, Zhixiang;* Dong, Guangbin.* “Rh-Catalyzed Decarbonylation of Conjugated Ynones via Carbon−Alkyne Bond Activation: Reaction Scope and Mechanistic Exploration via DFT Calculations”. Chem. Sci. 20156, 3201-3210. [doi]

Top 25 most downloaded in Q2 2015! [link]


Invited article for Prof. Yoshiaki Nakao Tetrahedron Young Investigator Award
Zhou, Xuan; Zafar, Imran; Dong, Guangbin.* “Catalytic intramolecular decarbonylative coupling of 3-aminocyclobutenones and alkenes: a unique approach to [3.1.0] bicycles”. Tetrahedron 201571, 4478-4483. [doi]


Zeng, Rong; Dong, Guangbin.* “Rh-Catalyzed Decarbonylative Cycloaddition with Alkynes via C−C Activation of Isatins”.J. Am. Chem. Soc2015137, 1408–1411. [doi]

Publications in 2014


Book Volume
“C−C Bond activation”. Topics in Current Chemistry 2014, V 346. Editor: Guangbin Dong. [doi]

With contributions by the groups of Prof. William D. Jones, Prof. Yoshiaki Nakao, Prof. Chul-Ho Jun, Prof. Christopher J. Douglas, Prof. Jason S. Kingsbury, Prof. Nicolai Cramer and Prof. Zhi-Xiang Yu.


Invited review
Huang, Zhongxing; Dong, Guangbin.* “Catalytic C−C Bond Forming Transformations via Direct β-C−H Functionalization of Carbonyl Compounds”. Tetrahedron Lett2014, 55, 5869–5889. [doi]


VIP in Angewandte Chemie
Zhao, Yu; Ding, Yu; Song, Jie; Li, Gang; Dong, Guangbin; Goodenough, John B.; Yu, Guihua.* “Sustainable Electrical Energy Storage through the Ferrocene/Ferrocenium Redox Reaction in Aprotic Electrolyte”. Angew. Chem. Int. Ed. 2014,53, 11036–11040. [doi]


Xu, Tao; Dong, Guangbin.* “Coupling of Sterically Hindered Trisubstituted Olefins and Benzocyclobutenones by C–C Activation: Total Synthesis and Structural Revision of Cycloinumakiol”. Angew. Chem., Int. Ed. 201453, 10733–10736. [doi]


Thompson, S. John; Dong, Guangbin.* “Alkylation of Rhodium Porphyrins Using Ammonium and Quinolinium Salts”.Organometallics 201433, 3757–3767. [doi]


Ko, Haye Min; Dong, Guangbin.* “Cooperative activation of cyclobutanones and olefins leads to bridged ring systems by a catalytic [4 + 2] coupling”. Nature Chemistry 20146, 739–744. [doi]


Mo, Fanyang; Dong, Guangbin.* “Regioselective ketone α-alkylation with simple olefins via dual activation”. Science, 2014345, 68–72. [doi]

*Highlighted by Chemical & Engineering News 2014, 92(27), 6. Ketones Couple With Olefins In Alkylation Advance


Invited article for 2014 Emerging Investigators issue:
Wang, Zhiqian; Reinus, Brandon J.; Dong, Guangbin.* “Catalytic intermolecular β-C–H alkenylation of α-enamino-ketones with simple alkynes”. Chem. Common201450, 5230–5232. [doi]


Invited article for Prof. Sarah Reisman Tetrahedron Young Investigator Award:
Chen, Penghao; Savage, Nikolas A.; Dong, Guangbin.* “Concise synthesis of functionalized benzocyclobutenones”. Tetrahedron 201470, 4135–4146. [doi]


Invited Review:
Dermenci, Alpay; Coe, Jotham W.; Dong, Guangbin.* “Direct Activation of Relatively Unstrained Carbon-Carbon Bonds in Homogenous Systems”.Organic Chemistry Frontiers 20141, 567–581. [doi]

Top 3 most-read articles in Aug. 2013. [link]


Invited Review:
Mo, Fanyang; Tabor, John; Dong, Guangbin.* “Alcohols or Masked Alcohols as Directing Groups for C–H Bond Functionalization”. Chem. Lett. 2014, 43, 264–271. [doi]


Xu, Tao; Savage, Nikolas A.; Dong, Guangbin.* “Rhodium(I)-Catalyzed Decarbonylative Spirocyclization through C-C Bond Cleavage of Benzocyclobutenones: An Efficient Approach to Functionalized Spirocycles”. Angew. Chem., Int. Ed. 201453, 1891–1895. [doi]


VIP in Angewandte Chemie
Chen, Peng-hao; Xu, Tao; Dong, Guangbin.* “Divergent Syntheses of Fused β-Naphthol and Indene Scaffolds Using Rhodium-Catalyzed Direct and Decarbonylative Alkyne–Benzocyclobutenone Couplings”. Angew. Chem., Int. Ed. 2014,53, 1674–1678. [doi]

*Highlighted by Synfacts 2014; 10(5): 0469.


Pan, Ming; Gong, Jinlong; Dong, Guangbin; Mullins, C. Buddie.* “Model Studies with Gold: A Versatile Oxidation and Hydrogenation Catalyst”. Acc. Chem. Res201447, 750–760. [doi]


Publications in 2013


Dong, Zhe; Dong, Guangbin.* “Ortho vs Ipso: Site-Selective Pd and Norbornene-Catalyzed Arene C-H Amination Using Aryl Halides”. J. Am. Chem. Soc. 2013135, 18350–18353. [doi]

Most read articles in Dec. 2013.
*Highlighted by Org. Process Res. Dev. 2014, 18, 362.
*Highlighted by Organic Chemistry Portal 2014 June16.


Huang, Zhongxing; Dong, Guangbin.* “Catalytic Direct β-Arylation of Simple Ketones with Aryl Iodides”. J. Am. Chem. Soc. 2013135, 17747-17750. [doi]

Top 1 most read articles in Dec. 2013.
*Highlighted by Synform 2014-03.
*Highlighted by Chemical & Engineering News 2013, 91, 28.
*Highlighted by Organic Chemistry Portal 2014 Sep 08.

Metal Duo Makes β-Aryl Ketones

The carbons immediately adjacent to a carbonyl group are usually straightforward places to form new carbon-carbon bonds. Just use a strong base, or a carefully designed catalyst, and that α-carbon is good to go. The next carbon over, the β-carbon, is not so amenable to change, however. Traditionally, β-substituted carbonyls require multiple steps to prepare. Because that β-motif is common in insecticides and drug candidates, chemists are keen to simplify the process. They’ve developed a handful of β-functionalization reactions, but none is generally applicable yet. Now, graduate student Zhongxing Huang and assistant professor Guangbin Dong of the University of Texas, Austin, have added to the toolbox with a reaction that inserts aromatic rings at the β-position of simple ketones (J. Am. Chem. Soc. 2013, DOI: 10.1021/ja410389a). The palladium-catalyzed process uses readily available aryl iodides and bromides as the substrates. A silver salt regenerates the active catalyst. Dong cautions that the reaction is still in its infancy. He’d like to figure out the reaction mechanism and replace the silver reagent with something less expensive. UT Austin is pursuing a provisional patent on the chemistry.

Chemical & Engineering News
ISSN 0009-2347
Copyright © 2013 American Chemical Society


Invited Review:
Mo, Fanyang; Dong, Guangbin;* Zhang, Yan; Wang, Jianbo.* “Recent Applications of Arene Diazonium Salts in Organic Synthesis”.Org. Biomol. Chem. 201311, 1582-2593. [doi]


Invited Review: 
Dermenci, Alpay; Dong, Guangbin.* “Decarbonylative C-C bond forming reactions mediated by transition metals”. Sci. China, Chem2013, 685-701. [doi]

*Awarded the 2013 best paper award by Science China Chemistry.


Dermenci, Alpay; Whittaker, Rachel; Dong, Guangbin.* “Rh(I)-Catalyzed Decarbonylation of Diynones via C-C Activation: Orthogonal Synthesis of Conjugated-Diynes”. Org. Lett201315, 2242. [doi]

*Highlighted by SYNFACTS issue 07/13.


Invited Highlights: 
Dong, Guangbin.* “Ketone-Based Transition-Metal-Catalyzed Carbon–Carbon and Carbon–Hydrogen Bond Activation: Exploratory Studies”. Synlett201324, 1. [doi]


Publications in 2012


Xu, Tao; Ko, Haye Min; Savage, Nikolas; Dong, Guangbin.* ” Highly Enantioselective Rh-Catalyzed Carboacylation of Olefins: Efficient Syntheses of Chiral Poly-Fused Rings “. J. Am. Chem. Soc. 2012134, 20005. [doi]


Mo, Fanyang; Trzepkowski, Louis J.; Dong, Guangbin.* “Synthesis of ortho-Acylphenols via Pd-Catalyzed Ketone-Directed Hydroxylation of Arenes”. Angew. Chem., Int. Ed. 201251, 13075. [doi]


Ren, Zhi; Mo, Fanyang; Dong, Guangbin.* “Catalytic Functionalization of Unactivated sp3 C–H Bonds via exo-Directing Groups: Synthesis of Chemically Differentiated 1,2-Diols”. J. Am. Chem. Soc. 2012134, 16991. [doi]

The third most read JACS article in Nov 2012.
*Highlighted by Nature Chemistry 2014, 6, 94-96.


Pan, Ming; Brush, Adrian; Dong, Guangbin; Mullins, C. Buddie.* “Tunable Ether Production via Coupling of Aldehydes or Aldehyde/Alcohol over Hydrogen-Modified Gold Catalysts at Low Temperatures” The Journal of Physical Chemistry Letters20123, 2512. [doi]


Wang, Zhiqian; Reinus, Brandon; Dong, Guangbin.* “Catalytic Intermolecular C-Alkylation of 1,2-Diketones with Simple Olefins: A Recyclable Directing Group Strategy”. J. Am. Chem. Soc. 2012134, 13954. [doi]


Teo. Peili; Wickens, Zachary K.; Dong, Guangbin; Grubbs, Robert H.* “Efficient and Highly Aldehyde Selective Wacker Oxidation.” Organic Letters201214, 3237. [doi]


Xu, Tao; Dong, Guangbin.* “Rh-Catalyzed Regioselective Carboacylation of Olefins: A C-C Activation Approach to Access Fused-Ring Systems.” Angew. Chem., Int. Ed. 201251, 7567. [doi]

*Highlighted by Chemical & Engineering News, 90(27), July 02, 2012
Cut-And-Sew Route Makes Fused Rings.

The work also presents a new twist on carbon-carbon bond activation. Chemists typically forge alkaloid core structures with lengthy multistep syntheses. Now, assistant professor Guangbin Dong and postdoctoral researcher Tao Xu have stitched the three-ring cores together in one rhodium-catalyzed step.


Trost, Barry M.*; Osipov, Maksim.; Dong , Guangbin. “Palladium-Catalyzed Asymmetric Allylic Alkylation of Electron-Deficient Pyrroles with Meso Electrophiles” Organic Letters201214, 2254. [doi]


Publications before 2011


Dong, Guangbin; Teo, Peili; Wickens, Zachary, K.; Grubbs, Robert H.* “Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration-like Process via Triple Relay Catalysis” Science2011, 333(6049), 1609-1612. [doi]

*Highlighted by Chemical & Engineering News, 89(38), September 19, 2011
Rule breaking Leads to Primary Alcohols. “One-pot reaction circumvents classic tenet governing additions to double bonds” By linking three processes in one pot, chemists have taken a step toward a greener alternative to hydroboration/oxidation, the classic two-step method for forming primary alcohols from alkenes (Science, DOI: 10.1126/science.1208685 To find a catalytic alternative, Caltech’s Robert H. Grubbs , Guangbin Dong , Peili Teo, and Zachary K. Wickens had to override Markovnikov’s rule, which dictates that a proton should end up on the less substituted alkene carbon, forming a secondary alcohol instead of the desired primary alcohol.
*Highlighted by CHEMCATCHEM, DOI: 10.1002/cctc.201100407

The search for anti-Markovnikov: The catalytic anti-Markovnikov hydration of terminal alkenes: how can it be done? Robert H. Grubbs et al. have partially answered this question. To design multiple coupled catalytic cycles is a complex endeavor, which is discussed here in the context of recent results. Increasingly mild coupled redox reactions look to help solve this intrinsic problem.


Trost, Barry M.;* Ngai, Ming-Yu; Dong, Guangbin “Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents” Organic Letters201113, 1900-1903. [doi]


Trost, Barry M.;* Frontier, Alison J.; Thiel, Oliver R.; Yang, Hanbiao; Dong, Guangbin “Total Syntheses of Bryostatins. Methods Developments: Atom-Economic and Stereoselective Synthesis of C-ring Subunit” Chemistry – A European Journal201117, 9762-9776. [doi]


Trost, Barry M.;* Yang, Hanbiao; Brindle, Cheyenne S.; Dong, Guangbin “Atom-Economic and Stereoselective Syntheses of the Ring A and B Subunits of the Bryostatins” Chemistry – A European Journal201117, 9777-9788. [doi]


Trost, Barry M.;* Yang, Hanbiao, Dong, Guangbin “Total Syntheses of Bryostatins. Syntheses of Two Ring-Expanded Bryostatin Analogues and Development of a New-Generation Strategy to Access the C7-C27 Fragment” Chemistry – A European Journal201117, 9789-9805. [doi]


Trost, Barry M.;* Dong, Guangbin “Total Synthesis of Bryostatin 16 using a Pd-Catalyzed Diyne-coupling as Macrocyclization Method and Synthesis of C20-epi-Bryostatin 7 as a Potent Anticancer Agent” Journal of the American Chemical Society2010132, 16403–16416. [doi]


Dong, Guangbin* “A Historical Story on the Synthesis of Agelastatin” Pure and Applied Chemistry201082, 2231-2246 (2010 IUPAC Prize for Young Chemists, invited review). [doi]


Trost, Barry M.;* Osipov, Maksim; Dong, Guangbin “Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Vinyl Aziridines with Nitrogen Heterocycles: Rapid Access to Biologically Active Pyrroles and Indoles” Journal of the American Chemical Society2010132, 15800–15807. [doi]


Trost, Barry M.;* Osipov, Maksim; Dong, Guangbin “A Concise Enantioselective Synthesis of (–)- Ranirestat.” Organic Letters201012, 1276-1279. [doi]


Trost, Barry M.;* Dong, Guangbin; Vance, Jennifer A. “Cyclic 1,2-Diketones as Core Building Blocks: A Strategy for the Total Synthesis of (–)-Terpestacin.” Chemistry – A European Journal201016, 6265-6277. [doi]


Trost, Barry M.;* Dong, Guangbin “A Stereodivergent Strategy to Both Product Enantiomers from the Same Enantiomer of A Stereoinducing Catalyst: Agelastatin A.” Chemistry – A European Journal200915, 6910-6919. [doi]


Trost, Barry M.;* Dong, Guangbin “Total Synthesis of Bryostatin 16 Using Atom Economical and Chemoselective Approaches.” Nature2008456, 485-488. [doi]

Highlighted by Angewandte Chemie International Edition (200948, 3221-3223) [doi]Chemical and Engineering News(20088, 11) [doi], Chemistry World of Royal Chemical Society (200827 November) and Nature (2008456, 451-453.)[doi]


Dong, Guangbin* “Hosomi–Sakurai Reaction” Vol. 3, 139-180; Modern Organic Reactions, Hu, Yuefei; Lin, Guoqiang Eds, Chemical Industry Press: Beijing, 2008.


Trost, Barry M.;* Dong, Guangbin “Asymmetric Annulation toward Pyrrolo-piperazinones. Concise Enantioselective Syntheses of Pyrrole Alkaloid Natural Products.” Organic Letters20079, 2357-2359. [doi]


Trost, Barry M.;* Dong, Guangbin; Vance, Jennifer A. “A Diosphenol-Based Strategy for the Total Synthesis of (–)-Terpestacin.” Journal of the American Chemical Society2007129, 4540-4541. [doi]


Trost, Barry M.;* Dong, Guangbin “New Class of Nucleophiles for Palladium-Catalyzed Asymmetric Allylic Alkylation. Total Synthesis of Agelastatin A.” Journal of the American Chemical Society2006128, 6054-6055. [doi]


Tang, Yefeng; Deng, Lujiang; Zhang, Yandong; Dong, Guangbin; Chen, Jiahua;* Yang, Zhen* “Thioureas as Ligands in the Pd-Catalyzed Intramolecular Pauson-Khand Reaction.” Organic Letters20057, 1657-1659. [doi]


Tang, Yefeng; Deng, Lujiang; Zhang, Yandong; Dong, Guangbin; Chen, Jiahua;* Yang, Zhen* “Tetramethyl Thiourea/Co2(CO)8-Catalyzed Pauson-Khand Reaction under Balloon Pressure of CO.” Organic Letters20057, 593-595. [doi]


Dai, Mingji; Liang, Bo; Wang, Cuihua; You, Zejin; Xiang, Jing; Dong, Guangbin; Chen, Jiahua;* Yang, Zhen* “A Novel Thiourea Ligand Applied in the Pd-Catalyzed Heck, Suzuki and Suzuki Carbonylative Reactions.” Advanced Synthesis & Catalysis 2004346, 1669-1673. [doi]


Dai, Mingji; Wang, Cuihua; Dong, Guangbin; Xiang, Jing; Luo, Tuoping; Liang, Bo; Chen, Jiahua;* Yang, Zhen* “Development of Thiourea-based Ligands for the Pd-Catalyzed Bis(methoxy -carbonylation) of Terminal Olefins.”European Journal of Organic Chemistry200322, 4346-4348. [doi] 
* corresponding author


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