ArticleJournal of the American Chemical Society2018
Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Nickel-catalyzed domino annulation coupling to construct oxindole analogues: A mechanistic and synthetic investigation.iScience · 2025Article
- Iron(II) Phthalocyanine-Catalyzed Olefination of Aldehydes with Diazoacetonitrile: A Novel Approach to Construct Alkenyl Nitriles.ACS omega · 2024Article
- Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation.Nature communications · 2024Article
- C-H Bond Functionalization of N-Heteroarenes Mediated by Selectfluor.Topics in current chemistry (Cham) · 2023Review
- Selectfluor and TBAX (Cl, Br) Mediated Oxidative Chlorination and Bromination of Olefins.Organic letters · 2022Article
- The Morita-Baylis-Hillman reaction for non-electron-deficient olefins enabled by photoredox catalysis.Chemical science · 2022Article
- Aryl acrylonitriles synthesis enabled by palladium-catalyzed α-alkenylation of arylacetonitriles with vinyl halides/triflates.Frontiers in chemistry · 2022Article
- Copper(II)-Catalyzed Selective CFrontiers in chemistry · 2022Article
- Article
- Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes.Nature chemistry · 2020Article
- Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles.Angewandte Chemie (International ed. in English) · 2020Article
- E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis.Nature chemistry · 2019Article
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Authors and funding
8 authors.
Funding
Abstract
Nucleophilic attack on carbon-based electrophiles is a central reactivity paradigm in chemistry and biology. The steric and electronic properties of the electrophile dictate its reactivity with different nucleophiles of interest, allowing the opportunity to fine-tune electrophiles for use as coupling partners in multistep organic synthesis or for covalent modification of proteins in drug discovery. Reactions that directly transform inexpensive chemical feedstocks into versatile carbon electrophiles would therefore be highly enabling. Herein, we report the catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and a bystanding N-F oxidant to furnish branched alkenyl nitriles that are difficult to prepare using existing methods. We show that the alkenyl nitrile products serve as electrophilic reaction partners for both organic synthesis and the chemical proteomic discovery of covalent protein ligands.
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