Metal promoted conversion of aromatic amines to ortho-phenylenediimine derivatives by a radical coupling path?

Dalton Transactions Pub Date: 2020-02-18 DOI: 10.1039/D0DT00089B

Abstract

A radical path for the conversion of o-substituted arylamines to o-phenylenediimine derivatives is reported. In the presence of [RuII(PPh3)3Cl2] (RuP), 2-(phenylthio)aniline (LSNH2) acts as an o-amination agent. Reaction of LSNH2 with RuP in toluene promotes (4e + 4H+) oxidative dimerization affording an o-phenylenediimine complex of ruthenium(II). Similarly, intermolecular coupling between LSNH2 and other arylamines has been achieved.

Graphical abstract: Metal promoted conversion of aromatic amines to ortho-phenylenediimine derivatives by a radical coupling path
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