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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Primary Amide Directed Regioselective ortho-C-H-Arylation of (Aryl)Acetamides
Yogesh Jaiswal1, Yogesh Kumar1, Rima Thakur2
1Department of Chemistry, Indian Institute of Technology Patna , Bihta 801103, Bihar, India.
Abstract:
An efficient and regioselective palladium(II)-catalyzed primary acetamide assisted ortho arylation of arylacetamide has been discovered. This is the first report where functionalizable primary acetamide (-CH2CONH2) is used as a directing group for C(sp2)-H activation/cross-coupling reactions, circumventing the extra steps of installation and subsequent removal of the directing groups. The synthetic utility of this transformation is demonstrated through the scale-up synthesis. In addition, the primary acetamide can be manipulated into synthetically important derivatives such as nitriles and carboxylic acids.
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