Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: synthesis and tandem catalytic activity of the first PCS-pincer palladium complex

Chemistry : a European Journal
Marcella GagliardoKálmán J Szabó

Abstract

The synthesis and catalytic applications of a new aryl-based unsymmetrical PCS-pincer complex are reported. Preparation of the robust air- and moisture-stable PCS-pincer palladium complex 5[X] started from the symmetrical alpha,alpha'-dibromo-meta-xylene and involved the selective substitution of one bromide by PPh(2)(BH(3)), followed by substitution of the second bromide by SPh and subsequent introduction of the palladium. The new PCS complexes (5[X]) were employed as catalysts in two important organic transformations. Firstly, complex 5[Cl] displays high catalytic activity in aldol reactions but enters the catalytic cycle as a precatalyst. Secondly, complex 5[BF(4)] displays tandem catalytic activity in the coupling of allyl chlorides with aldehydes and imines in the presence of hexamethylditin. In these tandem catalytic reactions the first process is the conversion of allyl chlorides into trimethylallyltin (and trimethyltin chloride) with Sn(2)Me(6), which is followed by catalytic allylation of aldehyde and sulfonimine substrates. In addition, we present a new catalytic process for the one-pot allylation of 4-nitrobenzaldehyde with vinyloxirane. The catalytic performance of the novel PCS-pincer palladium complex was compared...Continue Reading

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Citations

May 7, 2016·Royal Society Open Science·Gavin W RoffeJohn Spencer
Jul 25, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Ginger E TysonMin Zhang
Mar 27, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Sarote BoonsengHazel Cox
Dec 9, 2014·Advanced Synthesis & Catalysis·Suravi ChakrabartyFraser F Fleming
May 14, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Paul BrunelDidier Bourissou
Feb 21, 2009·Chemistry : a European Journal·Sylvestre BonnetRobertus J M Klein Gebbink
Jul 7, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Niels J M PijnenburgRobertus J M Klein Gebbink
Jan 24, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Arun KumarAjai K Singh
Jun 15, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Lan-Chang LiangHon Man Lee
Aug 6, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Nicklas Selander, Kálmán J Szabó
Apr 9, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Noel NebraDidier Bourissou
Aug 22, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Arun KumarAjai K Singh
Nov 29, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Alberto Acosta-RamirezMatthias Bierenstiel
Oct 11, 2011·Chemical Communications : Chem Comm·Florence J WilliamsElizabeth R Jarvo
Mar 8, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Jun-Long NiuMao-Ping Song
Jul 9, 2010·Chemical Reviews·Anton V GulevichValentine G Nenajdenko
Nov 4, 2010·Journal of the American Chemical Society·Andrew G TennysonChristopher W Bielawski
Nov 23, 2010·Chemical Reviews·Nicklas Selander, Kálmán J Szabó

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