Stalling, T., Harker, W.R.R., Auvinet, A-L. et al. (2 more authors) (2015) Investigation of Alkyne Regioselectivity in the Ni-Catalyzed Benzannulation of Cyclobutenones. Chemistry - A European Journal, 21 (6). 2701 - 2704. ISSN 0947-6539
Abstract
A Ni-catalyzed benzannulation reaction of cyclobutenones and alkynes provides a rapid synthesis of heavily substituted phenols. The regioselectivity of this reaction can be modulated by variation of substituents on the alkyne. Though the incorporation of Lewis basic donors provides modest selectivities, the use of aryl substituents can provide high levels of regiocontrol. Finally, alkynylboronates derived from alkyl-substituted acetylenes provide both high yields and regioselectivities. This study suggests that alkynes bearing one sp2- and one sp3-based substituent can undergo benzannulation with high levels of regiocontrol whereby the sp3-based group is incorporated ortho-to the phenolic OH.
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: | catalysis; cycloadditions; nickel; phenols; regioselectivity |
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: | 01 Oct 2015 15:38 |
Last Modified: | 21 Mar 2018 09:24 |
Published Version: | http://dx.doi.org/10.1002/chem.201405863 |
Status: | Published |
Publisher: | Wiley |
Refereed: | Yes |
Identification Number: | 10.1002/chem.201405863 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:90394 |