ArticleAngewandte Chemie (International ed. in English)2022
Explaining Regiodivergent Vinylations with Vinylbenziodoxolones.
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.
- Acidity Controlled Formal Nucleophilic Substitution of Hydrofluoroolefin-Based Iodonium Salt with O-nucleophiles: Synthetic Application and Mechanistic Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Rh-Catalyzed Enantioselective Aryl C-H Bond Cyclopropylation.Journal of the American Chemical Society · 2025Article
- Structure-reactivity analysis of novel hypervalent iodine reagents inFrontiers in chemistry · 2024Article
- Three-componentBeilstein journal of organic chemistry · 2024Article
- Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications.Molecules (Basel, Switzerland) · 2023Review
- Explaining Regiodivergent Vinylations with Vinylbenziodoxolones.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Vinylbenziodoxolones have recently been identified as efficient hypervalent iodine(III) reagents for electrophilic vinylations under transition metal-free conditions. Their unique reactivity allows synthesis of either internal or terminal alkenes, depending on the nucleophile class. This paper constitutes the first mechanistic investigation of VBX vinylations, and makes use of NMR studies, deuterium labelling and computations to rationalize the observed regio- and stereochemical outcome. Internal alkene formation in S-vinylation was found to proceed through the ligand coupling mechanism typical of diaryliodonium salts, whereas terminal alkene formation in P-vinylations took place via a phosphinous acid-coordinated VBX complex, which underwent concerted deprotonation and Michael-type addition. Subsequent base-assisted protonation and E2 elimination delivered the terminal alkene. The findings can be used to predict the regioselectivity in vinylations of other nucleophile classes.
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Registered trials
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