Visible-light-mediated direct difluoromethylation of alkynoates: synthesis of 3-difluoromethylated coumarins

A photoredox-catalyzed direct difluoromethylation of alkynoates has been developed. A well-designed photoredox system induces a single-step, regioselective installation of CF H onto alkynes. Difluoromethyl sulfone was used as an easy to handle CF H radical source to afford the desired 3-difluorometh...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (43), p.9057-9060
Main Authors: Zhu, Mei, Fu, Weijun, Wang, Zhiqiang, Xu, Chen, Ji, Baoming
Format: Article
Language:English
Subjects:
Alkynes
Chemical synthesis
Migration
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Summary:A photoredox-catalyzed direct difluoromethylation of alkynoates has been developed. A well-designed photoredox system induces a single-step, regioselective installation of CF H onto alkynes. Difluoromethyl sulfone was used as an easy to handle CF H radical source to afford the desired 3-difluoromethylated coumarins in moderate to good yields via a radical-triggered tandem difluoromethylation/5-exo cyclization/ester migration process.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02366a