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Tris(pentafluorophenyl)borane-catalyzed carbenium ion generation and autocatalytic pyrazole synthesis - a computational and experimental study

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Dasgupta, A, Babaahmadi, R, Pahar, S, Stefkova, K, Gierlichs, L, Yates, BF ORCID: 0000-0001-9663-3301, Ariafard, A ORCID: 0000-0003-2383-6380 and Melen, RL 2021 , 'Tris(pentafluorophenyl)borane-catalyzed carbenium ion generation and autocatalytic pyrazole synthesis - a computational and experimental study' , Angewandte Chemie - International Edition, vol. 60, no. 46 , pp. 24395-24399 , doi: 10.1002/anie.202109744.

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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 Type: Article
Authors/Creators:Dasgupta, A and Babaahmadi, R and Pahar, S and Stefkova, K and Gierlichs, L and Yates, BF and Ariafard, A and Melen, RL
Keywords: DFT calculations, bororane catalysis, reaction mechanism
Journal or Publication Title: Angewandte Chemie - International Edition
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 1433-7851
DOI / ID Number: 10.1002/anie.202109744
Copyright Information:

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.

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