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Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles

Nicholls, A.J.; Batsanov, A.S.; Baxendale, I.R.

Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles Thumbnail


Authors

A.J. Nicholls

A.S. Batsanov



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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