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

Eisenhofer, Anna and Wille, Uta and Koenig, Burkhard (2017) Nitrosonium-Mediated Phenol-Arene Cross-Coupling Involving Direct C-H Activation. AUSTRALIAN JOURNAL OF CHEMISTRY, 70 (4). pp. 407-412. ISSN 0004-9425, 1445-0038

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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 nitrate.

Item Type: Article
Uncontrolled Keywords: AROMATIC NITRATION; ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; NITROGEN-DIOXIDE; NO3 RADICALS; FORMIC-ACID; CHEMISTRY; CATION; FLUOROALCOHOLS; ACETONITRILE;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 12:57
Last Modified: 26 Feb 2019 15:01
URI: https://pred.uni-regensburg.de/id/eprint/52

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