Title: Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance
Authors : Bolliger, Jeanne L.
Frech, Christian M.
Published in : Chemistry - a European journal
Volume(Issue) : 16
Issue : 13
Pages : 4075
Pages to: 4081
Publisher / Ed. Institution : Wiley
Issue Date: 2010
License (according to publishing contract) : Licence according to publishing contract
Type of review: Peer review (Publication)
Language : English
Subjects : Catalysis; Cross-linking reagents; X-ray crystallography; Ligands; Molecular models; Nanoparticles; Organometallic compounds; Palladium; Phosphines; Stereoisomerism
Subject (DDC) : 540: Chemistry
Abstract: Dichloro-bis(aminophosphine) complexes are stable depot forms of palladium nanoparticles and have proved to be excellent Suzuki-Miyaura catalysts. Simple modifications of the ligand (and/or the addition of water to the reaction mixture) have allowed their formation to be controlled. Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium (3), the most active catalyst of the investigated systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1-1.2 equiv) of arylboronic acid at 80 degrees C in the presence of 0.2 mol % of the catalyst in technical grade toluene in flasks open to the air. Conversions of >95 % were generally achieved within only a few minutes. The reaction protocol presented herein is universally applicable. Side-products have only rarely been detected. The catalytic activities of the aminophosphine-based systems were found to be dramatically improved compared with their phosphine analogue as a result of significantly faster palladium nanoparticle formation. The decomposition products of the catalysts are dicyclohexylphosphinate, cyclohexylphosphonate, and phosphate, which can easily be separated from the coupling products, a great advantage when compared with non-water-soluble phosphine-based systems.
Departement: Life Sciences and Facility Management
Publication type: Article in scientific Journal
DOI : 10.1002/chem.200903309
ISSN: 0947-6539
URI: https://digitalcollection.zhaw.ch/handle/11475/10468
Appears in Collections:Publikationen Life Sciences und Facility Management

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