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150053 - Tris(pentafluorophenyl)borane-catalyzed carbenium.pdf (1.72 MB)

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

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posted on 2023-05-21, 07:39 authored by Dasgupta, A, Rasool Babaahmadi, Pahar, S, Stefkova, K, Gierlichs, L, Brian YatesBrian Yates, Alireza AriafardAlireza Ariafard, Melen, RL

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 %).

Funding

Australian Research Council

University of Wollongong

History

Publication title

Angewandte Chemie - International Edition

Volume

60

Issue

46

Pagination

24395-24399

ISSN

1433-7851

Department/School

Recruitment and International

Publisher

Wiley-V C H Verlag Gmbh

Place of publication

Po Box 10 11 61, Weinheim, Germany, D-69451

Rights 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.

Repository Status

  • Open

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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