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Updated: Jun 1, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Photoredox-Enabled Direct and Three-Component Difluoroalkylative Modification of N-Aryl Glycinates
Fangyuan Yu1, Daoyi Yang1, Yuanlin Yang1
1Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, Hubei 430074, China.
Abstract:
A Cu(I) photoredox-enabled reaction that selectively incorporates a difluoroalkyl group into N-aryl glycine derivatives has been established. Using a bench-stable [Ph3PCF2H]+Br- salt, the -CF2H group could be installed either directly on the α-carbon of the glycine backbone or in a three-component fashion using an alkene as a bridge. A series of glycine derivatives have been evaluated, providing access to diverse unnatural amino esters and dipeptides with a -CHF2 unit. The studies of the compatibility of other perfluorinated alkyl radical precursors showed that the selectivity of direct α-coupling is closely associated with the electronic property of the radical, while the three-component reaction works well in most cases.
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