ArticleAngewandte Chemie (International ed. in English)2020
Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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29 citing papers in PubMed, 125 citations in OpenAlex.
- Photocatalysts for the decarboxylation conversion of C(spRSC advances · 2026Review
- Structural engineering, BSA binding and computational analysis of isonipacotate based enzyme inhibitors containing 1,2,4-triazole.PloS one · 2026Article
- Air-Insensitive Sulfonylation Enabled by a MOF-Supported Nickel Photocatalyst.Small (Weinheim an der Bergstrasse, Germany) · 2025Article
- Nickel-photoredox catalysis: merging photons with metal catalysts for organic synthesis.RSC advances · 2025Review
- Unlocking Chromium Decarboxylative Ligand-to-Metal Charge Transfer: Efficient and Redox-Neutral Allylation of Aldehydes Using Carboxylic Acids.Journal of the American Chemical Society · 2025Article
- π-π stacking assisted regioselectivity regulation in palladium-catalyzed cyclization reactions: a theoretical study.RSC advances · 2024Article
- Carbosulfonylation of Alkynes: A Direct Conversion of sp-C to spOrganic letters · 2024Article
- Regio- and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes.Nature communications · 2024Article
- Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024Article
- High-Throughput Determination of Stern-Volmer Quenching Constants for Common Photocatalysts and Quenchers.ACS organic & inorganic Au · 2023Article
- Palladium-catalyzed intramolecular asymmetric hydrocyclopropanylation of alkynes: synthesis of cyclopropane-fused γ-lactams.Chemical science · 2023Article
- Ligand-controlled stereodivergent alkenylation of alkynes to access functionalized trans- and cis-1,3-dienes.Nature communications · 2023Article
- Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis.Accounts of chemical research · 2022Article
- Mechanistic dichotomy in the solvent dependent access toChemical science · 2022Article
- Excited-state palladium-catalysed reductive alkylation of imines: scope and mechanism.Chemical science · 2022Article
- Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry.Nature communications · 2022Article
- Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer.Nature communications · 2022Article
- Rapid access toChemical science · 2022Article
- Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis.Chemical reviews · 2022Review
- Regiodivergent sulfonylarylation of 1,3-enynesChemical science · 2021Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkynes are an important class of organic molecules due to their utility as versatile building blocks in synthesis. Although efforts have been devoted to the difunctionalization of alkynes, general and practical strategies for the direct hydroalkylation and alkylarylation of terminal alkynes under mild reaction conditions are less explored. Herein, we report a photoredox/nickel dual-catalyzed anti-Markovnikov-type hydroalkylation of terminal alkynes as well as a one-pot arylalkylation of alkynes with alkyl carboxylic acids and aryl bromides via a three-component cross-coupling. The results indicate that the transformations proceed via a new mechanism involving a single-electron transfer with subsequent energy-transfer activation pathways. Moreover, steady-state and time-resolved fluorescence-spectroscopy measurements, density functional theory (DFT) calculations, and wavefunction analysis have been performed to give an insight into the catalytic cycle.
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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.