Palladium Catalyzed Carbonylative Coupling for Synthesis of Arylketones and Arylesters Using Chloroform as the Carbon Monoxide Source

Poonam Sharma, Sandeep Rohilla and Nidhi Jain*

*Department of Chemistry, Indian Institute of Technology Delhi, New Delhi, India 110016, Email: njainchemistry.iitd.ac.in

P. Sharma, S. Rohilla, N. Jain, J. Org. Chem., 2017, 82, 1105-1113.

DOI: 10.1021/acs.joc.6b02711

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Abstract

The use of CHCl₃ as a convenient and safe carbonyl source in the presence of KOH enables a modular, palladium catalyzed synthesis of aryl(hetero)aryl benzophenones and aryl benzoates from aryl(hetero)aryl halides via an initial carbonylation to generate an aroyl halide, which undergoes coupling with arylboronic acids, boronates, and phenols. Direct carbonylative coupling of indoles at the third position has also been accomplished.

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proposed mechanism

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Key Words

aryl ketones, multicomponent reactions

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ID: J42-Y2017