ArticleNature communications2024
Stereospecific syn-dihalogenations and regiodivergent syn-interhalogenation of alkenes via vicinal double electrophilic activation strategy.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Enriching AlkeneOrganic letters · 2026Article
- Unlocking azole chemical space via modular and regioselective N-alkylation.Nature chemistry · 2025Article
- Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.Angewandte Chemie (International ed. in English) · 2025Article
- Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.Communications chemistry · 2024Article
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Authors and funding
4 authors.
Funding
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Abstract
Whereas the conventional anti-dihalogenation of alkenes is a valuable synthetic tool with highly predictable stereospecificity, the restricted reaction mechanism makes it challenging to alter the diastereochemical course into the complementary syn-dihalogenation process. Only a few notable achievements were made recently by inverting one of the stereocenters after anti-addition using a carefully designed reagent system. Here, we report a conceptually distinctive strategy for the simultaneous double electrophilic activation of the two alkene carbons from the same side. Then, the resulting vicinal leaving groups can be displaced iteratively by nucleophilic halides to complete the syn-dihalogenation. For this purpose, thianthrenium dication is employed, and all possible combinations of chlorine and bromine are added onto internal alkenes successfully, particularly resulting in the syn-dibromination and the regiodivergent syn-bromochlorination.
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Registered trials
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