ArticleChemical science2023
Photochemical halogen-bonding assisted generation of vinyl and sulfur-centered radicals: stereoselective catalyst-free C(sp
Article in Chemical science, 2023. 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.
- Multicomponent Photochemical Assembly of C(spACS organic & inorganic Au · 2026Article
- Generalizing Vinyl Halide Cross-Coupling Reactions with Photoredox and Photoredox/Nickel Dual Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Advancements in visible-light-induced reactions via alkenyl radical intermediates.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Review
- Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides.Chemical science · 2023Article
- Radical approaches to C-S bonds.Nature reviews. Chemistry · 2023Review
- Shining light on halogen-bonding complexes: a catalyst-free activation mode of carbon-halogen bonds for the generation of carbon-centered radicals.Chemical science · 2023Review
Corrections and comments
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Authors and funding
2 authors.
Funding
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Abstract
The combination of photochemistry and halogen bonding interactions has risen in the last few years as a powerful synthetic tool for the creation of radical intermediates under mild conditions. In the formation of carbon-centered radicals, this reactivity has been to date restricted to the employment of aryl and alkyl halides as precursors. We now envisioned that the halogen-bonding initiated formation of highly reactive vinyl radicals would be a feasible process for the photochemical cross-coupling between thiols and alkenyl halides under basic conditions. The reaction shows indeed a very broad functional group tolerance, is stereoselective, simple and scalable. In-depth mechanistic studies point at the formation of vinyl and sulfur-centered radicals as the intermediates of the reaction and DFT calculations support the pre-formation of a halogen-bonding complex as the initiator of the photochemical transformation. Synthetic applications were developed to extend the utility of this methodology.
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Registered trials
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