ArticleBeilstein journal of organic chemistry2015
Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.
Article in Beilstein journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 33 citations in OpenAlex.
- Acid-Catalyzed Hydrothiolation ofThe Journal of organic chemistry · 2021Article
- Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.Angewandte Chemie (International ed. in English) · 2020Article
- A HF Loaded Lewis-Acidic Aluminium Chlorofluoride for Hydrofluorination Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif.Beilstein journal of organic chemistry · 2019Article
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2 authors at 1 institution in 1 country.
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Abstract
A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C-C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.
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