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

Handle URI:
http://hdl.handle.net/10754/561598
Title:
An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling
Authors:
Marziale, Alexander N.; Jantke, Dominik; Faul, Stefan Holger; Reiner, Thomas; Herdtweck, Eberhardt; Eppinger, Jorg ( 0000-0001-7886-7059 )
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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Biological & Organometallic Catalysis Laboratories
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Green Chem.
Issue Date:
2011
DOI:
10.1039/c0gc00522c
Type:
Article
ISSN:
14639262
Sponsors:
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.
Is Supplemented By:
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:http://hdl.handle.net/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:http://hdl.handle.net/10754/624623
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorMarziale, Alexander N.en
dc.contributor.authorJantke, Dominiken
dc.contributor.authorFaul, Stefan Holgeren
dc.contributor.authorReiner, Thomasen
dc.contributor.authorHerdtweck, Eberhardten
dc.contributor.authorEppinger, Jorgen
dc.date.accessioned2015-08-02T09:15:03Zen
dc.date.available2015-08-02T09:15:03Zen
dc.date.issued2011en
dc.identifier.issn14639262en
dc.identifier.doi10.1039/c0gc00522cen
dc.identifier.urihttp://hdl.handle.net/10754/561598en
dc.description.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.en
dc.description.sponsorshipWe 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.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleAn efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-couplingen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentBiological & Organometallic Catalysis Laboratoriesen
dc.identifier.journalGreen Chem.en
dc.contributor.institutionTechnischeUniversitätMünchen, DepartmentChemie, Lichtenbergstr. 4, D-85747 Garching, Germanyen
kaust.authorFaul, Stefan Holgeren
kaust.authorEppinger, Jorgen
kaust.authorMarziale, Alexander N.en
kaust.authorJantke, Dominiken
dc.relation.isSupplementedByMarziale, 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/ccvg2q2en
dc.relation.isSupplementedByDOI:10.5517/ccvg2q2en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624622en
dc.relation.isSupplementedByMarziale, 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/ccvg2r3en
dc.relation.isSupplementedByDOI:10.5517/ccvg2r3en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624623en
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