ArticleNature chemistry2020
Nickel-catalysed anti-Markovnikov hydroarylation of unactivated alkenes with unactivated arenes facilitated by non-covalent interactions.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
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48 citing papers in PubMed.
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- Pillar[5]arene-catalyzed anti-Markovnikov halogenations through cationic intermediates stabilization in confined spaces.Nature communications · 2026Article
- Rhodium-Catalyzed Arene Alkenylation Using Benzoquinone Derivatives as Oxidants.Organometallics · 2026Article
- Additive-Controlled Regioswitching in Ni-Catalyzed Enantioselective Hydrophosphination of Unactivated Alkenes.Journal of the American Chemical Society · 2026Article
- Nickel-catalyzed β-arylation and benzylation of 2'-hydroxychalcones to access warfarin analogues.Communications chemistry · 2025Article
- Chiral Imidazo[1,5‑JACS Au · 2025Article
- Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.Angewandte Chemie (International ed. in English) · 2025Article
- Remote Migratory Reductive Arylation of Unactivated Alkenes Enabled by Electrochemical Nickel Catalysis.ChemSusChem · 2025Article
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- Computational Library Enables Pattern Recognition of Noncovalent Interactions and Application as a Modern Linear Free Energy Relationship.The Journal of organic chemistry · 2024Article
- Reversible C-CN Bond Cleavage by a Formal Dinickel(I) Hydride Cation.Organometallics · 2024Article
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- IPr*Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Practical and regioselective halonitrooxylation of olefins to access β-halonitrates.Nature communications · 2024Article
- Hexa-Fe(III) Carboxylate Complexes Facilitate Aerobic Hydrocarbon Oxidative Functionalization: Rh Catalyzed Oxidative Coupling of Benzene and Ethylene to Form Styrene.ACS catalysis · 2024Article
- Rhodium-Catalyzed Oxidative Alkenylation of Anisole: Control of Regioselectivity.Organometallics · 2024Article
- Highly Anti-Markovnikov Selective Oxidative Arene Alkenylation Using Ir(I) Catalyst Precursors and Cu(II) Carboxylates.Organometallics · 2024Article
- Cooperative HNature chemistry · 2024Article
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6 authors.
Funding
Abstract
Anti-Markovnikov additions to alkenes have been a longstanding goal of catalysis, and anti-Markovnikov addition of arenes to alkenes would produce alkylarenes that are distinct from those formed by acid-catalysed processes. Existing hydroarylations are either directed or occur with low reactivity and low regioselectivity for the n-alkylarene. Herein, we report the first undirected hydroarylation of unactivated alkenes with unactivated arenes that occurs with high regioselectivity for the anti-Markovnikov product. The reaction occurs with a nickel catalyst ligated by a highly sterically hindered N-heterocyclic carbene. Catalytically relevant arene- and alkene-bound nickel complexes have been characterized, and the rate-limiting step was shown to be reductive elimination to form the C-C bond. Density functional theory calculations, combined with second-generation absolutely localized molecular orbital energy decomposition analysis, suggest that the difference in activity between catalysts containing large and small carbenes results more from stabilizing intramolecular non-covalent interactions in the secondary coordination sphere than from steric hindrance.
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