Comas-Barcelo, J., Foster, R.S., Fiser, B. et al. (2 more authors) (2015) Cu-Promoted Sydnone Cycloadditions of Alkynes: Scope and Mechanism Studies. Chemistry - A European Journal, 21 (8). 3257 - 3263. ISSN 0947-6539
Abstract
Cu salts have been found to promote the cycloaddition reaction of sydnones and terminal alkynes, providing significant reduction in reaction times. Specifically, the use of Cu(OTf)2 is found to provide 1,3-disubstituted pyrazoles, whereas simply switching the promoter system to Cu(OAc)2 allows the corresponding 1,4-isomers to be produced. The mechanism of the Cu-effect in each case has been investigated by experimental and theoretical studies, and they suggest that Cu(OTf)2 functions by Lewis acid activation of the sydnone, whereas Cu(OAc)2 promotes formation of reactive CuI acetylides.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author produced version of a paper subsequently published in Chemistry - A European Journal. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | cycloadditions; density functional calculations; pyrazole; regioselective reactions; sydnones |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 02 Oct 2015 14:26 |
Last Modified: | 23 Mar 2018 12:34 |
Published Version: | http://dx.doi.org/10.1002/chem.201406118 |
Status: | Published |
Publisher: | Wiley |
Refereed: | Yes |
Identification Number: | 10.1002/chem.201406118 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:90392 |