Difluoromethylthiolation of Phenols and Related Compounds with a HF 2 CSO 2 Na/Ph 2 PCl/Me 3 SiCl System

A novel HF CSO Na/Ph PCl/Me SiCl system is disclosed for the late-stage direct difluoromethylthiolation of C and C nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF H compounds in good yields. Other substr...

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Bibliographic Details
Published in:Organic letters 2017-02, Vol.19 (4), p.934-937
Main Authors: Huang, Zhongyan, Matsubara, Okiya, Jia, Shichong, Tokunaga, Etsuko, Shibata, Norio
Format: Article
Language:English
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Summary:A novel HF CSO Na/Ph PCl/Me SiCl system is disclosed for the late-stage direct difluoromethylthiolation of C and C nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00113