Thiosuccinimide enabled S-N bond formation to access N -sulfenylated sulfonamide derivatives with synthetic diversity

A thiosuccinimide enabled S-N cross-coupling strategy has been established for the intermolecular -sulfenylation of clinically approved sulfa drugs under additive-free conditions. This approach features simple operation, high chemoselectivity for sulfenylating the phenylamino group of sulfonamides,...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-01, Vol.22 (5), p.990-997
Main Authors: Wang, Peifeng, Li, Shan, Wen, Huiling, Lei, Yin, Huang, Shujuan, Wang, Zixiu, Su, Jialong, Guan, Wenxiang, Lei, Jian
Format: Article
Language:English
Subjects:
Cross coupling
Methylation
Oxidation
Substrates
Sulfonamides
Thiols
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Summary:A thiosuccinimide enabled S-N cross-coupling strategy has been established for the intermolecular -sulfenylation of clinically approved sulfa drugs under additive-free conditions. This approach features simple operation, high chemoselectivity for sulfenylating the phenylamino group of sulfonamides, wide substrate scope, and easy scale production, affording -sulfenylated products in moderate to excellent yields (up to 90%). In addition, we also found that this transformation can be realized in a one-pot manner by employing readily available thiols as starting materials, and the obtained sulfonamide derivatives are capable of various late-stage functionalizations, including oxidation, arylation, benzylation, and methylation.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01848b