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The Synthesis and Utility of Metal-Nitrosophenolato Compounds—Highlighting the Baudisch Reaction
Article

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

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK
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Molecules 2019, 24(22), 4154; https://doi.org/10.3390/molecules24224154
Received: 14 October 2019 / Revised: 13 November 2019 / Accepted: 14 November 2019 / Published: 16 November 2019
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. View Full-Text
Keywords: copper-nitrosophenolato complex; phenols; C-nitrosation; sodium nitrite; copper; cycloaddition; heterocyclic; ambient conditions copper-nitrosophenolato complex; phenols; C-nitrosation; sodium nitrite; copper; cycloaddition; heterocyclic; ambient conditions
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MDPI and ACS Style

Nicholls, A.J.; Batsanov, A.S.; Baxendale, I.R. Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles. Molecules 2019, 24, 4154. https://doi.org/10.3390/molecules24224154

AMA Style

Nicholls AJ, Batsanov AS, Baxendale IR. Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles. Molecules. 2019; 24(22):4154. https://doi.org/10.3390/molecules24224154

Chicago/Turabian Style

Nicholls, Alexander J., Andrei S. Batsanov, and Ian R. Baxendale 2019. "Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles" Molecules 24, no. 22: 4154. https://doi.org/10.3390/molecules24224154

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