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Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds

Dasgupta, A, Stefkova, K, Babaahmadi, R, Gierlichs, L, Ariafard, A ORCID: 0000-0003-2383-6380 and Melen, RL 2020 , 'Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds' , Angewandte Chemie, vol. 59, no. 36 , pp. 15492-15496 , doi:

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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 were used to elucidate the mechanism for this alkenylation reaction.

Item Type: Article
Authors/Creators:Dasgupta, A and Stefkova, K and Babaahmadi, R and Gierlichs, L and Ariafard, A and Melen, RL
Keywords: alkenylation, diazoesters, metal-free catalysis, tris(pentafluorophenyl)borane, DFT
Journal or Publication Title: Angewandte Chemie
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 1433-7851
DOI / ID Number:
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Copyright 2020 The Authors. Licensed under Creative Commons Attribution 4.0 International (CC BY 4.0)

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