title: Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.
abstract: 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.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China; 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.
authors.forename: Bing
authors.initials: B
authors.lastname: Zheng
authors.affiliation: 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.
authors.forename: Minyan
authors.initials: M
authors.lastname: Li
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
authors.forename: Gui
authors.initials: G
authors.lastname: Gao
authors.affiliation: 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; Department of Chemistry, University of Pierre and Marie Curie, Paris 75005, France.
authors.forename: Yuying
authors.initials: Y
authors.lastname: He
authors.affiliation: 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.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
keywords: Palladium-catalyzed; aryl chloride; arylation; sulfonamide; sumatriptan