An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling
AuthorsMarziale, Alexander N.
Faul, Stefan Holger
KAUST DepartmentBiological & Organometallic Catalysis Laboratories
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Permanent link to this recordhttp://hdl.handle.net/10754/561598
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AbstractThe 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.
SponsorsWe 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.
PublisherRoyal Society of Chemistry (RSC)
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Marziale, A. N., Jantke, D., Faul, S. H., Reiner, T., Herdtweck, E., & Eppinger, J. (2011). CCDC 788104: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvg2q2. DOI: 10.5517/ccvg2q2 HANDLE: 10754/624622
Marziale, A. N., Jantke, D., Faul, S. H., Reiner, T., Herdtweck, E., & Eppinger, J. (2011). CCDC 788105: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvg2r3. DOI: 10.5517/ccvg2r3 HANDLE: 10754/624623