ArticleNature chemistry2024
Diastereodivergent nucleophile-nucleophile alkene chlorofluorination.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 citing papers in PubMed.
- Fluorination of amino-quinones enhances anti-RSC medicinal chemistry · 2026Article
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Alternating-Polarity Electrolysis Enables Efficient Enantioselective Semipinacol Rearrangement Using Sodium Chloride.Journal of the American Chemical Society · 2026Article
- Enriching AlkeneOrganic letters · 2026Article
- Non-Aqueous Binary and TernaryJournal 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
- General Alkene 1,2-Journal of the American Chemical Society · 2024Article
- Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.Communications chemistry · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The selective hetero-dihalogenation of alkenes provides useful building blocks for a broad range of chemical applications. Unlike homo-dihalogenation, selective hetero-dihalogenation reactions, especially fluorohalogenation, are underdeveloped. Current approaches combine an electrophilic halogen source with a nucleophilic halogen source, which necessarily leads to anti-addition, and regioselectivity has only been achieved using highly activated alkenes. Here we describe an alternative, nucleophile-nucleophile approach that adds chloride and fluoride ions over unactivated alkenes in a highly regio-, chemo- and diastereoselective manner. A curious switch in the reaction mechanism was discovered, which triggers a complete reversal of the diastereoselectivity to promote either anti- or syn-addition. The conditions are demonstrated on an array of pharmaceutically relevant compounds, and detailed mechanistic studies reveal the selectivity and the switch between the syn- and anti-diastereomers are based on different active iodanes and which of the two halides adds first.
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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.