Palladium-Catalyzed Oxidative Carboacetoxylation of Activated Alkynes with Amino Acids

Abstract A palladium-catalyzed intramolecular oxidative carboacetoxylation reaction of alkynes with various amino acids has been demonstrated for the first time, forming pharmaceutically important 3-methyleneindolin-2-one. In the presence of Pd(OAc)2 and ArI(OAc)2, N-arylpropiolamides underwent tandem acetoxypalladation/C-H functionalization reactions with various Boc-amino acids to form corresponding methyleneindolin-2-ones bearing amino acid motifs in moderate to excellent yields. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]