Issue 9, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Hiroyuki Kawai,a   Zhe Yuan,a   Etsuko Tokunagaa  and  Norio Shibata*a  

* Corresponding authors

a Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp
Fax: (+) 81-52-735-5442

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

DOI
https://doi.org/10.1039/C3OB27368G
Article type
Communication
Submitted
26 Nov 2012
Accepted
14 Jan 2013
First published
14 Jan 2013

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

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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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