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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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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)
Deposited By:College Office - CoSE
Deposited On:2022-05-16
Last Modified:2022-05-18
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