ArticleNature chemistry2022
Stereodefined alkenes with a fluoro-chloro terminus as a uniquely enabling compound class.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 40 citations in OpenAlex.
- Asymmetric synthesis of alkyl fluoridesGreen chemistry : an international journal and green chemistry resource : GC · 2026Article
- Article
- Synthesis and Characterization of anInorganic chemistry · 2026Article
- Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review.Beilstein journal of organic chemistry · 2026Review
- Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes.Angewandte Chemie (International ed. in English) · 2025Article
- Application of Asymmetric Catalysis in theJournal of the American Chemical Society · 2025Article
- Applications of Olefin Metathesis in the Synthesis of Fluorinated Substrates and Design of Fluorinated Catalysts.Topics in current chemistry (Cham) · 2025Review
- Synthesis ofJournal of the American Chemical Society · 2024Article
- Revisiting the Potential of Group VI Inorganic Precatalysts for the Ethenolysis of Fatty Acids through a Mechanochemical Approach.ACS omega · 2024Article
- 2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones.Organic letters · 2023Article
- Catalytic Cross-Metathesis Reactions That AffordJournal of the American Chemical Society · 2023Article
Corrections and comments
- Erratum issued
Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Trisubstituted alkenyl fluorides are important compounds for drug discovery, agrochemical development and materials science. Despite notable progress, however, many stereochemically defined trisubstituted fluoroalkenes either cannot be prepared efficiently or can only be accessed in one isomeric form. Here we outline a general solution to this problem by first unveiling a practical, widely applicable and catalytic strategy for stereodivergent synthesis of olefins bearing a fluoro-chloro terminus. This has been accomplished by cross-metathesis between two trisubstituted olefins, one of which is a purchasable but scarcely utilized trihaloalkene. Subsequent cross-coupling can then be used to generate an assortment of trisubstituted alkenyl fluorides. The importance of the advance is highlighted by syntheses of, among others, a fluoronematic liquid-crystal component, peptide analogues bearing an E- or a Z-amide bond mimic, and all four stereoisomers of difluororumenic ester (an anti-cancer compound).
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.