Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Adv Synth Catal

Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

Published: June 2016

A Palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald type precatalyst formed with Kwong's indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5218594PMC
http://dx.doi.org/10.1002/adsc.201600090DOI Listing

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