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Triarylborane-catalysed alkenylation reaction of aryl esters with diazo compounds

Dasgupta, Ayan, Stefkova, Katarína, Babaahmadi, Rasool, Gierlichs, Lukas, Ariafard, Alireza and Melen, Rebecca 2020. Triarylborane-catalysed alkenylation reaction of aryl esters with diazo compounds. Angewandte Chemie International Edition 59 (36) , pp. 15492-15496. 10.1002/anie.202007176

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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 have been undertaken to elucidate the mechanism for this alkenylation reaction.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Wiley
ISSN: 1433-7851
Funders: EPSRC
Date of First Compliant Deposit: 15 June 2020
Date of Acceptance: 2 June 2020
Last Modified: 08 Sep 2020 12:05

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