Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF Bond Cleavage.

J Org Chem

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering , Hunan University, Changsha 410082 , P. R. China.

Published: May 2019

AI Article Synopsis

  • The reaction involves trifluoroacetyl amides reacting with Grignard reagents, replacing the CF group with various alkyl or aryl groups.
  • A range of functional groups and halogens like F, Cl, and Br are compatible in this process.
  • The reaction likely goes through an isocyanate intermediate or a combination of alkoxide and amide intermediates.

Article Abstract

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.

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http://dx.doi.org/10.1021/acs.joc.9b00583DOI Listing

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