Issue 1, 2006

One-pot Pd/C catalysed ‘domino’ HALEX and Sonogashira reactions: a ligand- and Cu-free alternative

Abstract

The advantages of combining heterogeneous catalysis and aryl chloride substrates for cross-coupling are introduced. A heterogeneous Pd/C catalyst is used for activating aryl bromides and electron withdrawing aryl chlorides via a one-pot ‘domino’ HALEX–Sonogashira reaction. No ligand or co-catalyst is required, and the cross-coupling products are obtained in moderate to good yields. The influence of the solvent, base, iodide source and catalyst is evaluated. The catalyst is reusable for at least six consecutive reaction cycles. A variation on this reaction using catalytic amounts of KI is also proposed.

Graphical abstract: One-pot Pd/C catalysed ‘domino’ HALEX and Sonogashira reactions: a ligand- and Cu-free alternative

Article information

Article type
Paper
Submitted
23 Sep 2005
Accepted
02 Nov 2005
First published
23 Nov 2005

Org. Biomol. Chem., 2006,4, 111-115

One-pot Pd/C catalysed ‘domino’ HALEX and Sonogashira reactions: a ligand- and Cu-free alternative

M. B. Thathagar and G. Rothenberg, Org. Biomol. Chem., 2006, 4, 111 DOI: 10.1039/B513450A

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