Issue 2, 2014

Reactivity of C–H bonds of polychlorobenzenes for palladium-catalysed direct arylations with aryl bromides

Abstract

The reactivity of polychlorobenzenes vs. polyfluorobenzenes for palladium-catalysed direct arylation was studied. The PdCl(C3H5)(dppb)/KOAc system was found to promote the direct arylation of some polychlorobenzenes with aryl bromides. However, the reactivity of polychlorobenzenes was found to be lower than that of polyfluorobenzenes. The best yields were obtained from the coupling of 1,2,4,5-tetrachlorobenzene or 1,3,5-trichlorobenzene with electron-deficient aryl bromides. The C3 arylation of 2,5-dichlorothiophene was also found to proceed nicely.

Graphical abstract: Reactivity of C–H bonds of polychlorobenzenes for palladium-catalysed direct arylations with aryl bromides

Article information

Article type
Paper
Submitted
02 Oct 2013
Accepted
05 Nov 2013
First published
06 Nov 2013

Catal. Sci. Technol., 2014,4, 352-360

Reactivity of C–H bonds of polychlorobenzenes for palladium-catalysed direct arylations with aryl bromides

L. Zhao, T. Yan, C. Bruneau and H. Doucet, Catal. Sci. Technol., 2014, 4, 352 DOI: 10.1039/C3CY00757J

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