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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 Statement
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 |
| Downloads: | 3 View Download Statistics |
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