Palladium-Catalyzed Decarboxylative ortho-Acylation of Benzamides with α-Oxocarboxylic Acids.

J Org Chem

CAS Key Laboratory of Soft Matter Chemistry, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

Published: December 2017

A palladium-catalyzed decarboxylative ortho-acylation of tertiary benzamides with α-oxocarboxylic acids by weak O-coordination has been described. This reaction proceeds smoothly with a high monoacylation selectivity, affording ortho-acylated benzamides in moderate to good yields. When secondary benzamides are employed as the substrates, the formed ortho-acylated benzamides undergo further intramolecular cyclization to provide isoindolinone derivatives. In addition, several transformations of the synthesized ortho-acylated benzamides into a diversity of synthetically valuable products have been demonstrated.

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Source
http://dx.doi.org/10.1021/acs.joc.7b02552DOI Listing

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