Harrity, J.P.A., Lakeland, C.P. and Watson, D.W. (2020) Exploiting synergistic catalysis for an ambient temperature photocycloaddition to pyrazoles. Chemistry – A European Journal, 26 (1). pp. 155-159. ISSN 0947-6539
Abstract
Sydnone based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.
Metadata
Authors/Creators: |
|
||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Copyright, Publisher and Additional Information: | © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of a paper subsequently published in Chemistry. Uploaded in accordance with the publisher's self-archiving policy. | ||||||||||||||||||||||||||||||||||||||
Keywords: | enamines; pyrazoles; sydnones; photosensitisation; organocatalysis | ||||||||||||||||||||||||||||||||||||||
Dates: |
|
||||||||||||||||||||||||||||||||||||||
Institution: | The University of Sheffield | ||||||||||||||||||||||||||||||||||||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||||||||||||||||||||||||||||||||||||
Funding Information: |
|
||||||||||||||||||||||||||||||||||||||
Depositing User: | Symplectic Sheffield | ||||||||||||||||||||||||||||||||||||||
Date Deposited: | 30 Oct 2019 11:17 | ||||||||||||||||||||||||||||||||||||||
Last Modified: | 17 Dec 2021 10:06 | ||||||||||||||||||||||||||||||||||||||
Status: | Published | ||||||||||||||||||||||||||||||||||||||
Publisher: | Wiley | ||||||||||||||||||||||||||||||||||||||
Refereed: | Yes | ||||||||||||||||||||||||||||||||||||||
Identification Number: | https://doi.org/10.1002/chem.201904210 | ||||||||||||||||||||||||||||||||||||||
Related URLs: |