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Borane catalyzed selective diazo cross-coupling towards pyrazoles

Dasgupta, Ayan, Pahar, Sanjukta, Babaahmadi, Rasool, Gierlichs, Lukas, Yates, Brian F., Ariafard, Alireza and Melen, Rebecca L. 2022. Borane catalyzed selective diazo cross-coupling towards pyrazoles. Advanced Synthesis & Catalysis 364 (4) , pp. 773-780. 10.1002/adsc.202101312

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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.

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: 1615-4150
Funders: EPSRC
Date of First Compliant Deposit: 10 December 2021
Date of Acceptance: 25 November 2021
Last Modified: 30 Aug 2022 16:19

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