Palladium (II)-Salan Complexes as Catalysts for Suzuki-Miyaura C-C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance

Bunda, Szilvia and Voronova, Krisztina and Kathó, Ágnes and Udvardy, Antal and Joó, Ferenc (2020) Palladium (II)-Salan Complexes as Catalysts for Suzuki-Miyaura C-C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance. MOLECULES, 25 (17). ISSN 1420-3049

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Abstract

Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N'-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4](2-). Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki-Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 degrees C in water and air. A comparative study of the Pd (II)-sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst x h)(-1). The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.

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