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

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

Authors :
Jing K
Yao JP
Li ZY
Li QL
Lin HS
Wang GW
Source :
The Journal of organic chemistry [J Org Chem] 2017 Dec 01; Vol. 82 (23), pp. 12715-12725. Date of Electronic Publication: 2017 Nov 21.
Publication Year :
2017

Abstract

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
82
Issue :
23
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
29124923
Full Text :
https://doi.org/10.1021/acs.joc.7b02552