Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions

Bolliger, Jeanne L.; Frech, Christian M.

doi:10.1002/adsc.200900112

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DC Field	Value	Language
dc.contributor.author	Bolliger, Jeanne L.	-
dc.contributor.author	Frech, Christian M.	-
dc.date.accessioned	2018-09-12T13:56:47Z	-
dc.date.available	2018-09-12T13:56:47Z	-
dc.date.issued	2009	-
dc.identifier.issn	1615-4150	de_CH
dc.identifier.issn	1615-4169	de_CH
dc.identifier.uri	https://digitalcollection.zhaw.ch/handle/11475/10479	-
dc.description.abstract	Sequential addition of 1,1′,1′′‐phosphinetriyltripiperidine and 1,3‐diaminobenzene or resorcinol to toluene solutions of (cyclooctadiene)palladium dichloride [Pd(cod)(Cl)2] under nitrogen in “one pot” almost quantitatively yielded the aminophosphine‐based pincer complexes {[C6H3‐2,6‐(XP{piperidinyl}2)2]Pd(Cl)} (X=NH 1; X=O 2). Complex 1 (and to a minor extent 2) proved to be efficient Sonogashira catalysts, which allow the quantitative coupling of various electronically deactivated and/or sterically hindered and functionalized aryl iodides and aryl bromides with several alkynes as coupling partners within very short reaction times and low catalyst loadings. Importantly, in contrast to most of the Sonogashira catalysts, which either are both air‐ and moisture‐sensitive and/or require the addition of co‐catalysts, such as copper(I) iodide [CuI], for example, or a large excess of an amine, the coupling reactions were carried out without the use of amines, co‐catalysts or other aditives and without exclusion of air and moisture. Moreover, the desired products were exclusively formed (no side‐products were detected) without employing an excess of one of the substrates. Ethylene glycol and potassium phosphate (K3PO4) were found to be the ideal solvent and base for this transformation. Experimental observations strongly indicate that palladium nanoparticles are not the catalytically active form of 1 and 2. On the other hand, their transformation into another homogeneous catalytically active species cannot be excluded.	de_CH
dc.language.iso	en	de_CH
dc.publisher	Wiley	de_CH
dc.relation.ispartof	Advanced Synthesis & Catalysis	de_CH
dc.rights	Licence according to publishing contract	de_CH
dc.subject.ddc	540: Chemie	de_CH
dc.title	Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions	de_CH
dc.type	Beitrag in wissenschaftlicher Zeitschrift	de_CH
dcterms.type	Text	de_CH
zhaw.departement	Life Sciences und Facility Management	de_CH
dc.identifier.doi	10.1002/adsc.200900112	de_CH
zhaw.funding.eu	No	de_CH
zhaw.issue	6	de_CH
zhaw.originated.zhaw	No	de_CH
zhaw.pages.end	902	de_CH
zhaw.pages.start	891	de_CH
zhaw.publication.status	publishedVersion	de_CH
zhaw.volume	351	de_CH
zhaw.publication.review	Peer review (Publikation)	de_CH
Appears in collections:	Publikationen Life Sciences und Facility Management

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Bolliger, J. L., & Frech, Christian M. (2009). Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions. Advanced Synthesis & Catalysis, 351(6), 891–902. https://doi.org/10.1002/adsc.200900112

Bolliger, J.L. and Frech, Christian M. (2009) ‘Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions’, Advanced Synthesis & Catalysis, 351(6), pp. 891–902. Available at: https://doi.org/10.1002/adsc.200900112.

J. L. Bolliger and Christian M. Frech, “Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions,” Advanced Synthesis & Catalysis, vol. 351, no. 6, pp. 891–902, 2009, doi: 10.1002/adsc.200900112.

BOLLIGER, Jeanne L. und Christian M. FRECH, 2009. Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive- and amine-free reaction conditions. Advanced Synthesis & Catalysis. 2009. Bd. 351, Nr. 6, S. 891–902. DOI 10.1002/adsc.200900112

Bolliger, Jeanne L., and Christian M. Frech. 2009. “Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive- and Amine-Free Reaction Conditions.” Advanced Synthesis & Catalysis 351 (6): 891–902. https://doi.org/10.1002/adsc.200900112.

Bolliger, Jeanne L., and Christian M. Frech. “Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive- and Amine-Free Reaction Conditions.” Advanced Synthesis & Catalysis, vol. 351, no. 6, 2009, pp. 891–902, https://doi.org/10.1002/adsc.200900112.