Issue 9, 2013

A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform

Abstract

A simple strategy avoiding the decomposition of a naked trifluoromethyl anion to difluorocarbene by a sterically very demanding organo-superbase without the help of a trifluoromethyl anion reservoir such as DMF is reported. The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 base afforded trifluoromethyl alcohols in high yields.

Graphical abstract: A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform

Supplementary files

Article information

Article type
Communication
Submitted
26 Nov 2012
Accepted
14 Jan 2013
First published
14 Jan 2013

Org. Biomol. Chem., 2013,11, 1446-1450

A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform

H. Kawai, Z. Yuan, E. Tokunaga and N. Shibata, Org. Biomol. Chem., 2013, 11, 1446 DOI: 10.1039/C3OB27368G

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