A.J. Nicholls
Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles
Nicholls, A.J.; Batsanov, A.S.; Baxendale, I.R.
Abstract
A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature
Citation
Nicholls, A., Batsanov, A., & Baxendale, I. (2019). Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles. Molecules, 24(22), Article 4154. https://doi.org/10.3390/molecules24224154
Journal Article Type | Article |
---|---|
Acceptance Date | Nov 15, 2019 |
Online Publication Date | Nov 16, 2019 |
Publication Date | Nov 2, 2019 |
Deposit Date | Nov 16, 2019 |
Publicly Available Date | Nov 18, 2019 |
Journal | Molecules |
Electronic ISSN | 1420-3049 |
Publisher | MDPI |
Peer Reviewed | Peer Reviewed |
Volume | 24 |
Issue | 22 |
Article Number | 4154 |
DOI | https://doi.org/10.3390/molecules24224154 |
Public URL | https://durham-repository.worktribe.com/output/1283309 |
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Copyright Statement
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access
article distributed under the terms and conditions of the Creative Commons Attribution
(CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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