Citation: Fan Chen, Xiaoyu Zhao, Weihang Miao, Yingying Li, Ye Yuan, Lingling Chu. Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer[J]. Chinese Chemical Letters, ;2025, 36(5): 110239. doi: 10.1016/j.cclet.2024.110239 shu

Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai 201620, China

lingling.chu1@dhu.edu.cn

Received Date: 12 April 2024
Revised Date: 28 June 2024
Accepted Date: 10 July 2024
Available Online: 11 July 2024

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Here we present a highly efficient protocol utilizing nickel-hydride hydrogen atom transfer catalysis for the regio- and enantioselective hydrofluorination of internal alkenes. This method efficiently assembles a wide array of enantioenriched β-fluoro amides with excellent regio- and enantioselectivity from internal unactivated alkenes. Mechanistic investigations suggest that this transformation proceeds via a NiH-hydrogen atom transfer to alkene, followed by a stereoselective fluorine atom transfer process. The weak coordination effect of the tethered amide group is identified as a crucial factor governing the observed regio- and enantioselectivity.
- Alkenes,
- Hydrofluorination,
- Hydrogen atom transfer,
- Fluorine atom transfer,
- Nickel catalysis
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