Grayson, J. and Partridge, B.M. orcid.org/0000-0002-8550-9994 (2019) Mild Cu-catalyzed oxidation of benzylic boronic esters to ketones. ACS Catalysis, 9 (5). pp. 4296-4301. ISSN 2155-5435
Abstract
The oxidation of benzylic boronic esters directly to the ketone is reported. This mild Cu-catalyzed method uses an ambient atmosphere of air as the terminal oxidant and is notably chemoselective. Oxidation of the C-B bond occurs selectively, even in the presence of unprotected alcohols. Initial investigation suggests the reaction proceeds through an alkylboron to Cu transmetallation, peroxide formation, and rearrangement to give the carbonyl.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 American Chemical Society. This is an author-produced version of a paper subsequently published in ACS Catalysis. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Boron; catalysis; copper; ketones; oxidation |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number ROYAL SOCIETY RSG\R1\180065 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 11 Apr 2019 13:23 |
Last Modified: | 23 Nov 2021 10:47 |
Status: | Published |
Publisher: | American Chemical Society (ACS) |
Refereed: | Yes |
Identification Number: | 10.1021/acscatal.9b00992 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:144855 |