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

Alexander N. Marziale, Dominik Jantke, Stefan Holger Faul, Thomas Reiner, Eberhardt Herdtweck, Jörg Eppinger

Research output: Contribution to journalArticlepeer-review

98 Scopus citations

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. © 2011 The Royal Society of Chemistry.
Original languageEnglish (US)
Pages (from-to)169-177
Number of pages9
JournalGreen Chem.
Volume13
Issue number1
DOIs
StatePublished - 2011

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We are grateful to the Elitenetzwerk Bayern (graduate fellowship for A.N.M.), KAUST (graduate fellowship for A.N.M. and D.J.) and the IDK NanoCat for funding of this project. Experimental support by Markus Scheibel is gratefully acknowledged. Finally we are particularly grateful to the Aramco PMT team, KAUST HSE and KAUST Procurement, who all worked very hard for more than a year to finishing our research laboratories.

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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