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Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates.

ABSTRACT: A plethora of drug molecules and agrochemicals contain the sulfonamide functional group. However, sulfonamides are seldom viewed as synthetically useful functional groups. To confront this limitation, a late-stage functionalization strategy is described, which allows sulfonamides to be converted to pivotal sulfonyl radical intermediates. This methodology exploits a metal-free photocatalytic approach to access radical chemistry, which is harnessed by combining pharmaceutically relevant sulfonamides with an assortment of alkene fragments. Additionally, the sulfinate anion can be readily obtained, further broadening the options for sulfonamide functionalization. Mechanistic studies suggest that energy-transfer catalysis (EnT) is in operation.

SUBMITTER: Tilby MJ

PROVIDER: S-EPMC9127806 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates.

Tilby Michael J MJ Dewez Damien F DF Pantaine Loïc R E LRE Hall Adrian A Martínez-Lamenca Carolina C Willis Michael C MC

ACS catalysis 20220506 10

A plethora of drug molecules and agrochemicals contain the sulfonamide functional group. However, sulfonamides are seldom viewed as synthetically useful functional groups. To confront this limitation, a late-stage functionalization strategy is described, which allows sulfonamides to be converted to pivotal sulfonyl radical intermediates. This methodology exploits a metal-free photocatalytic approach to access radical chemistry, which is harnessed by combining pharmaceutically relevant sulfonamid ...[more]

PMID: 35633900

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