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 language | English (US) |
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Pages (from-to) | 169-177 |
Number of pages | 9 |
Journal | Green Chem. |
Volume | 13 |
Issue number | 1 |
DOIs | |
State | Published - 2011 |
ASJC Scopus subject areas
- Environmental Chemistry
- Pollution
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Datasets
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CCDC 788104: Experimental Crystal Structure Determination : bis(mu~2~-Chloro)-bis(hydrogen-bis(diphenylphosphinito-P,P')-palladium) dichloromethane solvate
Marziale, A. N. (Creator), Jantke, D. (Creator), Faul, S. H. (Creator), Reiner, T. (Creator), Herdtweck, E. (Creator) & Eppinger, J. (Creator), Dryad Digital Repository, 2011
DOI: 10.5517/ccvg2q2, http://hdl.handle.net/10754/624622
Dataset
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CCDC 788105: Experimental Crystal Structure Determination : bis(mu~2~-chloro)-bis(2-((diisopropylphosphino)oxy)biphenyl-3-yl)-di-palladium
Marziale, A. N. (Creator), Jantke, D. (Creator), Faul, S. H. (Creator), Reiner, T. (Creator), Herdtweck, E. (Creator) & Eppinger, J. (Creator), Dryad Digital Repository, 2011
DOI: 10.5517/ccvg2r3, http://hdl.handle.net/10754/624623
Dataset