Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 16, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202116071
Keywords
Alkynyl Radical; Alkynyl-Sulfonium Salt; Catalysis; Chalcogen Bonding; Chalcogenoacetylenes
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Funding
- National Natural Science Foundation of China [22001248, 22173103]
- Fundamental Research Funds for the Central Universities
- University of the Chinese Academy of Sciences
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Chalcogen bonding has emerged as a promising tool in organic synthesis, and this study reports the ChB catalysis of alkynyl-sulfonium salts for various ionic transformations. The photocapability of ChB is also demonstrated to generate alkynyl radicals.
Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well-developed selenium- and tellurium-based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl-sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1-diphenylethylene, nitro-Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise.
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