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Issue 43, 2010
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Solvent-free aromatic C–H functionalisation/halogenation reactions

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Abstract

The solvent-free, palladium-catalysed reaction of anilides with CuCl2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(II) chloride to yield the chlorinated anilide products.

Graphical abstract: Solvent-free aromatic C–H functionalisation/halogenation reactions

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Supplementary files

Article information


Submitted
28 Apr 2010
Accepted
18 Jun 2010
First published
08 Oct 2010

Dalton Trans., 2010,39, 10464-10472
Article type
Paper

Solvent-free aromatic C–H functionalisation/halogenation reactions

R. B. Bedford, J. U. Engelhart, M. F. Haddow, C. J. Mitchell and R. L. Webster, Dalton Trans., 2010, 39, 10464
DOI: 10.1039/C0DT00385A

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