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Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds

Citation

Dasgupta, A and Stefkova, K and Babaahmadi, R and Gierlichs, L and Ariafard, A and Melen, RL, Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds, Angewandte Chemie, 59, (36) pp. 15492-15496. ISSN 1433-7851 (2020) [Refereed Article]


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Copyright 2020 The Authors. Licensed under Creative Commons Attribution 4.0 International (CC BY 4.0) https://creativecommons.org/licenses/by/4.0/

DOI: doi:10.1002/anie.202007176

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.

Item Details

Item Type:Refereed Article
Keywords:tris(pentafluorophenyl)borane, alkenylation, diazoesters, DFT, metal-free catalysis
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Physical organic chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Babaahmadi, R (Mr Rasool Babaahmadi)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:142019
Year Published:2020
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:10
Deposited By:Chemistry
Deposited On:2020-12-08
Last Modified:2021-07-05
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