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

ABSTRACT: A Palladium-catalyzed ?-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.

SUBMITTER: Zheng B

PROVIDER: S-EPMC5218594 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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

Zheng Bing B Li Minyan M Gao Gui G He Yuying Y Walsh Patrick J PJ

Advanced synthesis & catalysis 20160615 13

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. ...[more]

PMID: 28070178

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