Fricero, P., Bialy, L., Brown, A.W. orcid.org/0000-0001-6279-5177 et al. (3 more authors) (2017) Synthesis and Modular Reactivity of Pyrazole 5-Trifluoroborates: Intermediates for the Preparation of Fully-Functionalized Pyrazoles. Journal of Organic Chemistry, 82 (3). pp. 1688-1696. ISSN 0022-3263
Abstract
The regioselective condensation of hydrazines and ynone trifluoroborates provides access to a range of pyrazole 5-trifluoroborates. The stability of the borate unit allows chemoselective halogenation of the heteroaromatic ring, thereby delivering pyrazole scaffolds that allow orthogonal functionalization at C5 and C4. The modular reactivity of these intermediates is exemplified by cross-coupling reactions, enabling regiocontrolled synthesis of fully-functionalized pyrazole derivatives.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 American Chemical Society. This is an author produced version of a paper subsequently published in Journal of Organic Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
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 EUROPEAN COMMISSION - FP6/FP7 COSSHNET - 606734 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 19 Jan 2017 12:50 |
Last Modified: | 30 Jun 2023 09:24 |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | Yes |
Identification Number: | 10.1021/acs.joc.6b02847 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:110751 |