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Expedient synthesis of ?-substituted fluoroethenes.

ABSTRACT: A mild and efficient synthesis of 1-aryl-1-fluoroethenes from benzothiazolyl (aryl)fluoromethyl sulfones and paraformaldehyde, under DBU- or Cs(2)CO(3)-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 ?-fluoroalkenes bearing electron-withdrawing functionalities is also shown.

SUBMITTER: Mandal SK

PROVIDER: S-EPMC3723398 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Expedient synthesis of α-substituted fluoroethenes.

Mandal Samir K SK Ghosh Arun K AK Kumar Rakesh R Zajc Barbara B

Organic & biomolecular chemistry 20120220 16

A mild and efficient synthesis of 1-aryl-1-fluoroethenes from benzothiazolyl (aryl)fluoromethyl sulfones and paraformaldehyde, under DBU- or Cs(2)CO(3)-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. ...[more]

PMID: 22349519

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