Charge-tagged polar phosphine ligands in Pd-catalysed reactions in aqueous and ionic media

van Zyl, VL; Muller, A; Williams, DBG

Charge-tagged polar phosphine ligands in Pd-catalysed reactions in aqueous and ionic media

van Zyl, VL Muller, A Williams, DBG

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Publication Type:: Journal Article
Citation:: Tetrahedron Letters, 2018, 59 (10), pp. 918 - 921
Issue Date:: 2018-03-07

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Field	Value	Language
dc.contributor.author	van Zyl, VL	en_US
dc.contributor.author	Muller, A	en_US
dc.contributor.author	Williams, DBG https://orcid.org/0000-0002-3703-6301	en_US
dc.date.available	2020-05-25T19:21:14Z
dc.date.issued	2018-03-07	en_US
dc.identifier.citation	Tetrahedron Letters, 2018, 59 (10), pp. 918 - 921	en_US
dc.identifier.issn	0040-4039	en_US
dc.identifier.uri	http://hdl.handle.net/10453/128403
dc.description.abstract	© 2018 Elsevier Ltd A new range of polar imidazolium and phosphate-containing ligands was synthesised from readily available starting materials in high yielding multi-step transformations. These ligands were used to generate Pd catalysts for Suzuki and Heck C–C coupling reactions in organic and organic/aqueous media. The catalysts performed well in aqueous media in the Suzuki reaction and less well in the Heck reaction, related to substrate solubility in the aqueous media. When moving to ionic liquids, the Heck reaction dramatically improved, especially in media compatible with the polar catalysts and the non-polar reagents. In all cases, the catalysts were stable to the formation of Pd black, a form of degradation that frequently befalls Pd catalysts. The catalysts could be successfully recycled without loss of activity.	en_US
dc.relation.ispartof	Tetrahedron Letters	en_US
dc.relation.isbasedon	10.1016/j.tetlet.2018.01.073	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Charge-tagged polar phosphine ligands in Pd-catalysed reactions in aqueous and ionic media	en_US
dc.type	Journal Article
utslib.citation.volume	10	en_US
utslib.citation.volume	59	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
utslib.copyright.status	open_access
pubs.issue	10	en_US
pubs.publication-status	Published	en_US
pubs.volume	59	en_US

Abstract:

© 2018 Elsevier Ltd A new range of polar imidazolium and phosphate-containing ligands was synthesised from readily available starting materials in high yielding multi-step transformations. These ligands were used to generate Pd catalysts for Suzuki and Heck C–C coupling reactions in organic and organic/aqueous media. The catalysts performed well in aqueous media in the Suzuki reaction and less well in the Heck reaction, related to substrate solubility in the aqueous media. When moving to ionic liquids, the Heck reaction dramatically improved, especially in media compatible with the polar catalysts and the non-polar reagents. In all cases, the catalysts were stable to the formation of Pd black, a form of degradation that frequently befalls Pd catalysts. The catalysts could be successfully recycled without loss of activity.

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http://hdl.handle.net/10453/128403