ArticleAngewandte Chemie (International ed. in English)2025
Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Formal Markovnikov Hydroazolation of Alkenes via Reductive Activation of Alkylthianthrenium Salts.Journal of the American Chemical Society · 2026Article
- A Unified Synthetic Approach to 2-Alkyl Azetidines, Oxetanes, Thietanes and Cyclobutanes from Unactivated Alkenes.Journal of the American Chemical Society · 2025Article
- Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.Angewandte Chemie (International ed. in English) · 2025Article
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8 authors.
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Abstract
The anti-Markovnikov hydrofunctionalization of terminal, unactivated olefins is an evergreen synthetic challenge in organic chemistry. Several direct and indirect anti-Markovnikov methods have been developed, ranging from the classical hydroboration/oxidation protocol to state-of-the-art photoredox catalytic, transition-metal-complex-catalyzed, and enzymatic procedures. Despite the ever-expanding suite of synthetic capabilities, these methods still have limited generality in their substrate scope, especially with nucleophiles. Herein, we show that terminal, unactivated olefins can be transformed into anti-Markovnikov products via an alkenyl thianthrenium intermediate that undergoes sequential hydride and nucleophile addition. The strategic advantage of this method lies in the ability to utilize a diverse array of oxidatively sensitive nucleophiles as reaction partners. This is accomplished through a mechanistically distinct, two-stage dication pool anti-Markovnikov approach, where separate oxidative olefin activation by thianthrenation is followed by the selective generation of a reactive alkyl thianthrenium salt.
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