ArticleAngewandte Chemie (International ed. in English)2016
Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Three Component Thio- and Carboboration of Alkynes: A Modular Route to Functionalised Bicyclic Boronates.Angewandte Chemie (International ed. in English) · 2026Article
- Metal-Free Electrophilic Borylative Cyclizations of Alkynes.Chemical record (New York, N.Y.) · 2026Review
- Sustainable Synthesis of Medicinally Important Heterocycles.Mini reviews in medicinal chemistry · 2025Review
- Metal-Free Temperature-Controlled Regiodivergent Borylative Cyclizations of Enynes: BClAngewandte Chemie (International ed. in English) · 2022Article
- Organophosphorus-catalyzed relay oxidation of H-Bpin: electrophilic C-H borylation of heteroarenes.Chemical science · 2020Article
- Selective oxymetalation of terminal alkynesChemical science · 2018Article
- Reactions of biologically inspired hydride sources with B(CPhilosophical transactions. Series A, Mathematical, physical, and engineering sciences · 2017Article
- Mechanistic Studies of Formal Thioboration Reactions of Alkynes.The Journal of organic chemistry · 2017Article
- BClAngewandte Chemie (International ed. in English) · 2017Article
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Authors and funding
4 authors.
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Abstract
The first ring-forming thioboration reaction of C-C π bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S-B σ bond formation, providing a mechanistically distinct pathway to the thioboration of C-C π bonds.
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Registered trials
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