Research Progress of α-Diazo Sulfonium Salts as Free Radicals and Multivariate Reactive Species Precursors

doi:10.6023/cjoc202512047

Abstract

α-Diazo sulfonium salts are a class of novel diazo reagents that have undergone rapid development in recent years. Under photoirradiation or metal-catalyzed systems, systematic and in-depth research progress has been achieved regarding the reactions of these compounds as precursors to various reactive intermediates, including α-diazomethyl radicals, carbyne radicals, ylide radicals, carbenes, electron donor-acceptor (EDA) complexes, and dicationic species. This review focuses on reviewing the generation mechanisms of various reactive intermediates based on α-diazo sulfonium salts, the types of organic synthesis reactions they participate in, and the corresponding reaction mechanisms. Finally, a summary and outlook are presented on the current development status and existing challenges in this field.

Key words: α-diazo sulfonium salts, novel diazo reagents, radicals, reactive intermediates

Cite this article

Xing Li, Ziqiang Zhang, Zhiyuan Lin, Jiacheng Yao, Xinyan Li, Qiangqiang Li, Jun Xuan. Research Progress of α-Diazo Sulfonium Salts as Free Radicals and Multivariate Reactive Species Precursors[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1376-1389.

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Fig. & Tab. 18

Scheme 1. Preparation of α-diazo sulfonium salt from hypervalent iodine compounds

Scheme 2. Preparation of α-diazo sulfonium salt with Tf2O

Scheme 3. Photoredox-catalyzed synthesis of triazoles from α-diazo sulfonium triflates

Scheme 5. Photoredox-catalyzed synthesis of α,α-diarylcycloalkenone compounds from α-diazo sulfonium triflates

Scheme 4. Photoredox-catalyzed synthesis of oxadiazole and pyrazole from α-diazo sulfonium triflates

Scheme 6. Photoredox-catalyzed synthesis of bis-dithiocarbamates and carbamates from α-diazo sulfonium triflates

Scheme 7. Photoredox-catalyzed modification of proteins with α-diazo sulfonium salt

Scheme 8. Photoredox-catalyzed synthesis of 1,4-dicarbonyl Z-alkenes from α-diazonium sulfonium trifluoromethanesulfonates via carbyne radical formation

Scheme 9. Photoredox-catalyzed synthesis of 3-difluoromethyl- pyrazole from α-diazodifluoroethyl sulfonium salt

Scheme 10. Photoredox-catalyzed synthesis of triazole from α-diazodifluoroethyl sulfonium salt

Scheme 11. Photoredox-catalyzed synthesis of oxadiazole from α-diazo sulfonium

Scheme 12. Rh-catalyzed synthesis of imidazo[1,5-a]quinoline from α-diazo sulfonium triflates and quinoline

Scheme 13. Rh-catalyzed synthesis of naphthalene from α-diazo sulfonium triflates and indene

Scheme 14. Rh-catalyzed synthesis of quinoline from α-diazo sulfonium triflates and indole

Scheme 15. Rh-catalyzed C—H/N—H functionalization of α-diazo sulfonium

Scheme 16. Photoredox-catalyzed synthesis of phenanthridine from α-diazo sulfonium triflates

Scheme 17. Synthesis of quinoline from α-diazo sulfonium triflates and α-ethylaniline

Scheme 18. Synthesis of glycine derivatives from amine compounds and α-diazo sulfonate triflates

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