A Route to α‑Fluoroalkyl Sulfides from α‑Fluoro­diaroyl­methanes

α,α-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating α-thioaryl-α,α-difluoro­aceto­phenones (Ar1COCF2SAr) and difluoro­methyl­thiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature....

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Bibliographic Details
Published in:Organic letters 2016-02, Vol.18 (3), p.592-595
Main Authors: Lin, Ya-mei, Yi, Wen-bin, Shen, Wan-zhao, Lu, Guo-ping
Format: Article
Language:English
Online Access:Get full text
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Summary:α,α-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating α-thioaryl-α,α-difluoro­aceto­phenones (Ar1COCF2SAr) and difluoro­methyl­thiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature. The method has also been extended to the synthesis of α-thioaryl-α-mono­fluoro­aceto­phenones using α-mono­fluoro­dibenzoyl­methane. Moreover, the benzoyl cation derived from α,α-difluoro­dibenzoyl­methane can react with nucleophiles to afford the desired products in a one-pot process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03654