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Updated: Jul 6, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Thiosuccinimide enabled S-N bond formation to access N-sulfenylated sulfonamide derivatives with synthetic diversity
Peifeng Wang1, Shan Li1, Huiling Wen1
1Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Disease of the Ministry of Education, Key Laboratory of Biomaterials and Biofabrication in Tissue Engineering of Jiangxi Province, College of Pharmacy, Gannan Medical University, Ganzhou 341000, PR China. zxw0001@gmu.edu.cn.
Abstract:
A thiosuccinimide enabled S-N cross-coupling strategy has been established for the intermolecular N-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 N-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.
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