Journal article

Nitrosonium-Mediated Phenol-Arene Cross-Coupling Involving Direct C-H Activation

Anna Eisenhofer, Uta Wille, Burkhard Koenig

AUSTRALIAN JOURNAL OF CHEMISTRY | CSIRO PUBLISHING | Published : 2017

Abstract

The nitrosonium ion (NO+) is a highly versatile nitration and nitrosation reagent, as well as a strong one-electron oxidant. Herein, we describe an environmentally benign and mild method for the in situ formation of NO+ from readily available inorganic nitrate salts, i.e. lithium nitrate, through a finely tuned interplay between formic acid and MeOH, which are used as the solvent system. This methodology was applied to the NO+-induced oxidative C-H activation of methoxy-substituted phenols, which are versatile lignin-derived aromatic feedstocks, to achieve C-C cross-coupling reactions with arenes. The regeneration of NO+ by atmospheric molecular oxygen enables substoichiometric use of the ni..

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University of Melbourne Researchers

Grants

Awarded by German Science Foundation (DFG)


Funding Acknowledgements

This work was financially supported by the German Science Foundation (DFG) (GRK 1626, Chemical Photocatalysis) and the German Academic Exchange Service (DAAD). A. E. thanks the Deutsche Bundesstiftung Umwelt (DBU) for a graduate scholarship.