ArticleJournal of the American Chemical Society2019
Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Reductive Cross-Coupling of Alkynes with Aryl Bromides via Zr/Pd Synergistic Catalysis.Organic letters · 2026Article
- Organic Peroxides in Transition-Metal-Free Cyclization and Coupling Reactions (C-C) via Oxidative Transformation.ACS omega · 2025Review
- Ni(0)-Catalyzed Efficient, Regioselective Synthesis of Dibenzo[ACS omega · 2024Article
- Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024Article
- Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes.ACS catalysis · 2023Article
- A General Strategy for the Asymmetric Preparation of α-Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride- and Palladium-Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Differential Dihydrofunctionalization: A Dual Catalytic Three-Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.Angewandte Chemie (International ed. in English) · 2022Article
- NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines.Nature communications · 2021Article
- Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products.Nature catalysis · 2020Article
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Authors and funding
2 authors.
Funding
Abstract
The differential dihydrofunctionalization of terminal alkynes is accomplished through the reductive three-component coupling of terminal alkynes, aryl halides, and pinacolborane. The transformation results in hydrofunctionalization of both π-bonds of an alkyne in a single reaction promoted by cooperative action of a copper/palladium catalyst system. The differential dihydrofunctionalization reaction has excellent substrate scope and can be accomplished in the presence of esters, nitriles, alkyl halides, epoxides, acetals, alkenes, aryl halides, and silyl ethers. Mechanistic experiments indicate that the reaction proceeds through copper-catalyzed hydroboration followed by a second hydrocupration. The resulting heterobimetallic complex is the key intermediate that participates in the subsequent palladium-catalyzed cross-coupling, which furnishes benzylic alkyl boronate products.
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