Citation: Zhi Zhou, Kaifeng Chen, Yi Wang, Xiuhua Zhong, Shuang Lin, Hui Gao, Wei Yi. Regiocontrolled Rh(Ⅲ)-catalyzed C–C coupling/C–N cyclization mediated by distinctive 1,2-migratory insertion of gem–difluoromethylene allenes: Reaction development and mechanistic insight[J]. Chinese Chemical Letters, ;2023, 34(5): 107849. doi: 10.1016/j.cclet.2022.107849 shu

Regiocontrolled Rh(Ⅲ)-catalyzed C–C coupling/C–N cyclization mediated by distinctive 1,2-migratory insertion of gem–difluoromethylene allenes: Reaction development and mechanistic insight

Zhi Zhou ^1, ,
Kaifeng Chen ¹ ,
Yi Wang ¹ ,
Xiuhua Zhong ,
Shuang Lin ,
Hui Gao ^*, ,
Wei Yi ^*,

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China

zhouzhi@gzhmu.edu.cn

gaoh9@gzhmu.edu.cn

yiwei@gzhmu.edu.cn

Received Date: 15 July 2022
Revised Date: 16 September 2022
Accepted Date: 22 September 2022
Available Online: 25 September 2022

Figures(6)

By developing gem–difluoromethylene allenes as viable partners, regiocontrolled Rh(Ⅲ)-catalyzed redox-neutral C–C coupling/C–N cyclization has been realized to build the pyridin-2(1H)-one motifs with the embedment of a Z-configured monofluoroalkene functionality, in which either (hetero)aromatic or vinylic amides were found to be compatible. Integrated experimental and computational mechanistic studies revealed that a tandem regioselective allene 1,2-insertion/β-H elimination/hydrogen transfer/oxidative addition/cyclization/cis-β-F elimination involving an unconventional Rh(Ⅲ)-Rh(Ⅰ)-Rh(Ⅲ) catalytic cycle accounts for the established transformation. Through further FMO analysis and IGMH maps, a non-covalent weak interaction network between the gem–difluoromethylene part and the OPiv moiety was rationally defined for the unconventional and specific regioselectivity control.
- Gem-difluoromethylene allenes,
- C-H functionalization,
- Regiocontrol,
- Rhodium(Ⅲ) catalysis,
- DFT calculations
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