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Issue 9, 2013
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A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform

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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

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Article information


Submitted
26 Nov 2012
Accepted
14 Jan 2013
First published
14 Jan 2013

Org. Biomol. Chem., 2013,11, 1446-1450
Article type
Communication

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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