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Tris(pentafluorophenyl)borane-catalyzed carbenium ion generation and autocatalytic pyrazole synthesis - a computational and experimental study
Citation
Dasgupta, A and Babaahmadi, R and Pahar, S and Stefkova, K and Gierlichs, L and Yates, BF and Ariafard, A and Melen, RL, Tris(pentafluorophenyl)borane-catalyzed carbenium ion generation and autocatalytic pyrazole synthesis - a computational and experimental study, Angewandte Chemie - International Edition, 60, (46) pp. 24395-24399. ISSN 1433-7851 (2021) [Refereed Article]
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Copyright Statement
2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution 4.0 International (CC BY 4.0) License, (https://creativecommons.org/licenses/by/4.0/) which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DOI: doi:10.1002/anie.202109744
Abstract
In recent years, metal-free organic synthesis using triarylboranes as catalysts has become a prevalent research area. Herein we report a comprehensive computational and experimental study for the highly selective synthesis of N-substituted pyrazoles through the generation of carbenium species from the reaction between aryl esters and vinyl diazoacetates in the presence of catalytic tris(pentafluorophenyl)borane [B(C6F5)3]. DFT studies were undertaken to illuminate the reaction mechanism revealing that the in situ generation of a carbenium species acts as an autocatalyst to prompt the regiospecific formation of N-substituted pyrazoles in good to excellent yields (up to 81 %).
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | DFT calculations, bororane catalysis, reaction mechanism |
| Research Division: | Chemical Sciences |
| Research Group: | Physical chemistry |
| Research Field: | Catalysis and mechanisms of reactions |
| 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: | Yates, BF (Professor Brian Yates) |
| UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
| ID Code: | 150053 |
| Year Published: | 2021 |
| Funding Support: | Australian Research Council (DP180100904) |
| Web of Science® Times Cited: | 6 |
| Deposited By: | College Office - CoSE |
| Deposited On: | 2022-05-16 |
| Last Modified: | 2022-08-19 |
| Downloads: | 5 View Download Statistics |
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