Issue 16, 2012

Expedient synthesis of α-substituted fluoroethenes

Abstract

A mild and efficient synthesis of 1-aryl-1-fluoroethenes from benzothiazolyl (aryl)fluoromethyl sulfones and paraformaldehyde, under DBU- or Cs2CO3-mediated conditions at room temperature, is described. A comparable diethyl fluoro(naphthalen-2-yl)methylphosphonate reagent does not react with paraformaldehyde under these mild conditions. The utility of the methodology for synthesis of terminal α-fluoroalkenes bearing electron-withdrawing functionalities is also shown.

Graphical abstract: Expedient synthesis of α-substituted fluoroethenes

Supplementary files

Article information

Article type
Communication
Submitted
05 Dec 2011
Accepted
25 Jan 2012
First published
20 Feb 2012

Org. Biomol. Chem., 2012,10, 3164-3167

Expedient synthesis of α-substituted fluoroethenes

S. K. Mandal, A. K. Ghosh, R. Kumar and B. Zajc, Org. Biomol. Chem., 2012, 10, 3164 DOI: 10.1039/C2OB07031F

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