Livingstone, K orcid.org/0000-0002-4169-3056, Bertrand, S, Kennedy, AR et al. (1 more author) (2020) Transition‐Metal‐Free Coupling of 1,3‐Dipoles and Boronic Acids as a Sustainable Approach to C−C Bond Formation. Chemistry – A European Journal, 26 (46). pp. 10591-10597. ISSN 0947-6539
Abstract
The need for alternative, complementary approaches to enable C−C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C−C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 The Authors. This is an open access article published under the terms of the Creative Commons Attribution License (CC-BY 4.0), which permits unrestricted use, distribution and reproduction in any medium, provided the original work is properly cited. |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 24 May 2023 16:04 |
Last Modified: | 24 May 2023 16:04 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/chem.202001590 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:197945 |