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Issue 1, 2011
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An efficient protocol for the palladium-catalysed Suzuki–Miyaura cross-coupling

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Abstract

The palladacyclic catalyst precursor received by ortho-palladation of ([1,1′-biphenyl]-2-yloxy)diisopropyl-phosphine represents a highly active system for Suzuki–Miyaura cross-coupling reactions when used in neat water. An efficient, broadly applicable and sustainable aqueous protocol was developed using 2.5 eq. of Na2CO3 as base, allowing the reaction to be performed under air and at ambient temperature with Pd loadings of 0.04 mol%. Coupling products are obtained in high yields and excellent purity by simple filtration with no organic solvents needed throughout the whole reaction. A broad variety of functional groups are tolerated and a large number of substrates can be applied with this protocol. The crystal structure of the palladacyclic catalyst precursor is presented as well as investigations targeting the nature of catalyst activation and the active catalytic species.

Graphical abstract: An efficient protocol for the palladium-catalysed Suzuki–Miyaura cross-coupling

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Supplementary files

Article information


Submitted
06 Sep 2010
Accepted
17 Nov 2010
First published
13 Dec 2010

Green Chem., 2011,13, 169-177
Article type
Paper

An efficient protocol for the palladium-catalysed Suzuki–Miyaura cross-coupling

A. N. Marziale, D. Jantke, S. H. Faul, T. Reiner, E. Herdtweck and J. Eppinger, Green Chem., 2011, 13, 169
DOI: 10.1039/C0GC00522C

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