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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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Publication details

The article was received on 06 Sep 2010, accepted on 17 Nov 2010 and first published on 13 Dec 2010


Article type: Paper
DOI: 10.1039/C0GC00522C
Citation: Green Chem., 2011,13, 169-177
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    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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