Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides

Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.

Automated summary

Redox-active benzimidazolium sulfonamides have been developed as thiolating reagents for reductive C-S bond coupling. The IMDN-SO2R reagent provides a stable cationic precursor to generate highly active N-S intermediates, enabling successful cross-electrophilic coupling with various organic halides. The use of an electrophilic sulfur source has practical benefits such as broad substrate scope and excellent tolerance, while avoiding catalyst deactivation and unpleasant odors from thiols.