Preview

PDF (Published version) 150053 - Tris(p...pdf | Download (1MB) | Preview

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:	https://doi.org/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.
Related URLs:	Google Scholar: Yates, BF UTAS Profile: Yates, BF Google Scholar: Ariafard, A UTAS Profile: Ariafard, A
Item Statistics:	View statistics for this item

Actions (login required)

Item Control Page