Dasgupta, Ayan, Pahar, Sanjukta, Babaahmadi, Rasool, Gierlichs, Lukas, Yates, Brian F., Ariafard, Alireza and Melen, Rebecca L.  ORCID: https://orcid.org/0000-0003-3142-2831
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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Abstract
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: | Schools > Chemistry Research Institutes & Centres > 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: | 24 May 2023 07:04 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/146076 |
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