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

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
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
Authors:	Bolliger, Jeanne L. Frech, Christian M.
DOI:	10.1002/adsc.200900112
Published in:	Advanced Synthesis & Catalysis
Volume(Issue):	351
Issue:	6
Page(s):	891
Pages to:	902
Issue Date:	2009
Publisher / Ed. Institution:	Wiley
ISSN:	1615-4150 1615-4169
Language:	English
Subject (DDC):	540: Chemistry
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.
URI:	https://digitalcollection.zhaw.ch/handle/11475/10479
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. (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.