Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 24, Pages 12499-12505Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02353
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- CSIR, New Delhi [02(0229)/15/EMR-II]
- Indian Institute of Technology (IIT) Patna
- IIT Patna
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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(sp(2))-Hactivation/crosscoupling 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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