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Issue 13, 2017

Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions

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Abstract

The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp2)–H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has first been carried out under electrochemical oxidative conditions. This versatile method for C–C bond formation between two aryl fragments can be realized under very mild potential-controlled oxidative conditions, and it does require neither incorporation of any halogen atoms or other leaving groups, nor the use of metal catalysts. The use of the electrochemical SHN methodology for modification of azaaromatic compounds has first been demonstrated.

Graphical abstract: Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions

Supplementary files

Article information


Submitted
14 Mar 2017
Accepted
28 Apr 2017
First published
28 Apr 2017

Green Chem., 2017,19, 2931-2935
Article type
Communication

Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions

O. N. Chupakhin, A. V. Shchepochkin and V. N. Charushin, Green Chem., 2017, 19, 2931 DOI: 10.1039/C7GC00789B

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