ArticleAngewandte Chemie (International ed. in English)2022
Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-Yne-Ene Coupling Reaction.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- An Initiator-Free Electrochemical Approach to Radical Thiol-Ene Coupling in a Microfluidic Reactor.Molecules (Basel, Switzerland) · 2026Article
- Phosphinothio(seleno)ation of alkynes/olefins and application on the late-stage functionalization of natural products.Communications chemistry · 2024Article
- Direct conversion of carboxylic acids to free thiolsChemical science · 2024Article
- Multicomponent Reactions between Heteroatom Compounds and Unsaturated Compounds in Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles.Chemical science · 2023Article
- Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-Yne-Ene Coupling Reaction.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The first example of an intermolecular thiol-yne-ene coupling reaction is reported for the one-pot construction of C-S and C-C bonds. Thiol-yne-ene coupling opens a new dimension in building molecular complexity to access densely functionalized products. The employment of Eosin Y/DBU/MeOH photocatalytic system suppresses hydrogen atom transfer (HAT) and associative reductant upconversion (via C-S three-electron σ-bond formation). Investigation of the reaction mechanism by combining online ESI-UHRMS, EPR spectroscopy, isotope labeling, determination of quantum yield, cyclic voltammetry, Stern-Volmer measurements and computational modeling revealed a unique photoredox cycle with four radical-involving stages. As a result, previously unavailable products of the thiol-yne-ene reaction were obtained in good yields with high selectivity. They can serve as stable precursors for synthesizing synthetically demanding activated 1,3-dienes.
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Registered trials
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