Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF2SO2Ph Reagent

A new difluoroalkylation reagent Sulfox-CF2SO2Ph bearing both sulfoximine and sulfone moieties was prepared from commercially available SulfoxFluor and PhSO2CF2H. On one hand, the Sulfox-CF2SO2Ph reagent could act as a (phenylsulfonyl)­difluoromethyl radical source under photoredox catalysis, in whi...

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Bibliographic Details
Published in:Organic letters 2024-02, Vol.26 (4), p.872-876
Main Authors: Li, Shali, Wang, Xiu, Yang, Yide, Ni, Chuanfa, Hu, Jinbo
Format: Article
Language:English
Online Access:Get full text
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Summary:A new difluoroalkylation reagent Sulfox-CF2SO2Ph bearing both sulfoximine and sulfone moieties was prepared from commercially available SulfoxFluor and PhSO2CF2H. On one hand, the Sulfox-CF2SO2Ph reagent could act as a (phenylsulfonyl)­difluoromethyl radical source under photoredox catalysis, in which the arylsulfoximidoyl group is selectively removed. On the other hand, under basic conditions, Sulfox-CF2SO2Ph could serve as a difluorocarbene precursor for S- and O-difluoromethylations with S- and O-nucleophiles, respectively, in which the phenylsulfonyl group in Sulfox-CF2SO2Ph is selectively removed (followed by α-elimination of the arylsulfoximidoyl group).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04116