Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
Abstract: Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal‐free alkenylation reactions of aryl esters with α‐diazoesters to give highly functionalized enyne products. Catalytic amounts of tris (pentafluorophenyl) borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds ; volume:59 ; number:36 ; year:2020 ; pages:15492-15496 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 36 (2020), 15492-15496 (gesamt 5)
- Creator
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Dasgupta, Ayan
Stefkova, Katarína
Babaahmadi, Rasool
Gierlichs, Lukas
Ariafard, Alireza
Melen, Rebecca L.
- DOI
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10.1002/anie.202007176
- URN
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urn:nbn:de:101:1-2022061312463763318783
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
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Associated
- Dasgupta, Ayan
- Stefkova, Katarína
- Babaahmadi, Rasool
- Gierlichs, Lukas
- Ariafard, Alireza
- Melen, Rebecca L.
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Gold-Catalyzed Cascade Cyclization of Diazo-tethered Alkynes
Iodine-catalyzed diazo activation to access radical reactivity
Copper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters
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Asymmetric Formal Insertion of Diazo Esters into Aryl–CHO Bonds
Palladium-catalyzed carbonylation reactions of aryl halides
Exploring the reactivity of α-triorganylsilyl [alpha-triorganylsilyl] α-diazo esters [alpha-diazo esters] : C-H activation, insertion reactions, and rearrangements
Brønsted acid‐catalyzed Reactions of Unprotected N‐heterocycles with Aryl/Aryl Diazoalkanes
Brønsted acid‐catalyzed Reactions of Unprotected N ‐heterocycles with Aryl/Aryl Diazoalkanes
Tunable Gold‐catalyzed Reactions of Propargyl Alcohols and Aryl Nucleophiles
Enantioselective Homologation of α-Keto Esters with α-Diazo Esters
Borane Catalyzed Selective Diazo Cross‐Coupling Towards Pyrazoles
Gold-Catalyzed Cascade Cyclization of Diazo-tethered Alkynes
Iodine-catalyzed diazo activation to access radical reactivity
Copper-catalyzed cascade reactions of α,β-unsaturated esters with keto esters