Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance

Bolliger, Jeanne L.; Frech, Christian M.

doi:10.1002/chem.200903309

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
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.
DOI:	10.1002/chem.200903309
Published in:	Chemistry - A European Journal
Volume(Issue):	16
Issue:	13
Page(s):	4075
Pages to:	4081
Issue Date:	2010
Publisher / Ed. Institution:	Wiley
ISSN:	0947-6539 1521-3765
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°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.
URI:	https://digitalcollection.zhaw.ch/handle/11475/10468
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Appears in collections:	Publikationen Life Sciences und Facility Management

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Bolliger, J. L., & Frech, Christian M. (2010). Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance. Chemistry - A European Journal, 16(13), 4075–4081. https://doi.org/10.1002/chem.200903309

Bolliger, J.L. and Frech, Christian M. (2010) ‘Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance’, Chemistry - A European Journal, 16(13), pp. 4075–4081. Available at: https://doi.org/10.1002/chem.200903309.

J. L. Bolliger and Christian M. Frech, “Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance,” Chemistry - A European Journal, vol. 16, no. 13, pp. 4075–4081, 2010, doi: 10.1002/chem.200903309.

BOLLIGER, Jeanne L. und Christian M. FRECH, 2010. Dichloro-bis(aminophosphine) complexes of palladium : highly convenient, reliable and extremely active Suzuki-Miyaura catalysts with excellent functional group tolerance. Chemistry - A European Journal. 2010. Bd. 16, Nr. 13, S. 4075–4081. DOI 10.1002/chem.200903309

Bolliger, Jeanne L., and Christian M. Frech. 2010. “Dichloro-Bis(aminophosphine) Complexes of Palladium : Highly Convenient, Reliable and Extremely Active Suzuki-Miyaura Catalysts with Excellent Functional Group Tolerance.” Chemistry - A European Journal 16 (13): 4075–81. https://doi.org/10.1002/chem.200903309.

Bolliger, Jeanne L., and Christian M. Frech. “Dichloro-Bis(aminophosphine) Complexes of Palladium : Highly Convenient, Reliable and Extremely Active Suzuki-Miyaura Catalysts with Excellent Functional Group Tolerance.” Chemistry - A European Journal, vol. 16, no. 13, 2010, pp. 4075–81, https://doi.org/10.1002/chem.200903309.