Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides

J Org Chem. 2013 Apr 19;78(8):4123-31. doi: 10.1021/jo400488q. Epub 2013 Apr 9.

Abstract

A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetamides / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Chloroacetates / chemistry*
  • Esters
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Indicators and Reagents / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Salts / chemistry*
  • Temperature

Substances

  • Acetamides
  • Boronic Acids
  • Chloroacetates
  • Esters
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Salts
  • chloroacetamide
  • Palladium