University Of Tasmania
150055 - Borane catalyzed selective diazo cross-coupling.pdf (4.35 MB)

Borane catalyzed selective diazo cross-coupling towards pyrazoles

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journal contribution
posted on 2023-05-21, 07:40 authored by Dasgupta, A, Pahar, S, Rasool BabaahmadiRasool Babaahmadi, Gierlichs, L, Brian YatesBrian Yates, Alireza AriafardAlireza Ariafard, Melen, RL

Decomposition of donor-acceptor diazo compounds leads to the formation of reactive carbene intermediates. These can undergo a wide variety of carbene transfer reactions to yield synthetically useful products. Herein, we report a selective borane catalyzed cyclization reaction from the combination of two different diazo compounds to afford N-substituted pyrazoles. The selective decomposition of the more reactive α-aryl α-diazoester and subsequent reaction with a vinyl diazoacetate produces N-alkylated pyrazoles in a regioselective manner. Catalytic amounts of tris(pentafluorophenyl)borane (10 mol%) were employed to afford the pyrazole products (36 examples) in yields from 59 to 80%. Extensive DFT studies have been undertaken to interpret the mechanism for this reaction which was found to go through two tandem catalytic cycles, both catalyzed by B(C6F5)3.


Australian Research Council

University of Wollongong


Publication title

Advanced Synthesis and Catalysis










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2021 The Authors. Advanced Synthesis & Catalysis 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, ( which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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