4.8 Article

Difluoromethylation of Carboxylic Acids via the Addition of Difluorinated Phosphorus Ylide to Acyl Chlorides

Journal

ORGANIC LETTERS
Volume 19, Issue 19, Pages 5304-5307

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02601

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Funding

  1. Russian Science Foundation [17-13-01041]
  2. Russian Science Foundation [17-13-01041] Funding Source: Russian Science Foundation

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A one-step protocol for the difluoromethylation of carboxylic acids is described. The reaction involves the interaction of intermediate acyl chlorides with in situ generated difluorinated phosphorus ylide Ph3P = CF2. Aromatic acids can be selectively transformed within one step either to bis-difluoromethylated alcohols or to difluorinated ketones depending on the particular reaction conditions. For bulky alpha-branched carboxylic acids, only ketones are produced.

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