Issue 35, 2016

Visible-light-initiated difluoromethylation of arene diazonium tetrafluoroborates

Abstract

A mild and efficient method for the radical addition of α-aryl-β,β-difluoroenol silyl with arene diazonium tetrafluoroborates at room temperature has been disclosed, which involves an innate radical long chain cycle, so only a small amount (0.05 mol%) of photocatalyst and a short light exposure time are required as radical initiators. A proposed mechanism for the transformation is also illustrated based on the results of control experiments and quantum calculations. A variety of α-aryl-α,α-difluoroketones were formed in moderate to high yields, and can be easily further transformed into various difluoromethylarenes under basic conditions.

Graphical abstract: Visible-light-initiated difluoromethylation of arene diazonium tetrafluoroborates

Supplementary files

Article information

Article type
Communication
Submitted
08 Jan 2016
Accepted
22 Mar 2016
First published
22 Mar 2016

Chem. Commun., 2016,52, 5965-5968

Visible-light-initiated difluoromethylation of arene diazonium tetrafluoroborates

Y. Wu, G. Lu, B. Zhou, M. Bu, L. Wan and C. Cai, Chem. Commun., 2016, 52, 5965 DOI: 10.1039/C6CC00177G

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