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

Dasgupta, Ayan, Babaahmadi, Rasool, Pahar, Sanjukta, Stefkova, Katarina, Gierlichs, Lukas, Yates, Brian F., Ariafard, Alireza and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2021. 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. 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
Date Type:	Publication
Status:	Published
Schools:	Chemistry Cardiff Catalysis Institute (CCI)
Additional Information:	This is an open access article under the terms of the Creative Commons Attribution License
Publisher:	Wiley
ISSN:	1433-7851
Funders:	EPSRC
Date of First Compliant Deposit:	18 October 2021
Date of Acceptance:	30 September 2021
Last Modified:	12 Aug 2023 03:43
URI:	https://orca.cardiff.ac.uk/id/eprint/144906

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