Journal
CHEMICAL SCIENCE
Volume 12, Issue 7, Pages 2509-2514Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc06446g
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Funding
- National Natural Science Foundation of China [21772085, 21971107]
- Fundamental Research Funds for the Central Universities [020514380220, 020514380131, 020514913412, 020514913214]
- Collaborative Innovation Center of Advanced Microstructures
- Jiangsu Provincial Key Laboratory of Photonic and Electronic Materials at Nanjing University
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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.
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.
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