Hydrogenation of α,β-unsaturated aldehydes in aqueous media with a water-soluble Pd(II)-sulfosalan complex catalyst

Gombos, Réka; Nagyházi, Brigitta; Joó, Ferenc

doi:10.1007/s11144-018-1488-8

Cited by 7 publications

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“…The exact reaction mechanism of the Suzuki–Miyaura cross-couplings catalysed by Pd (II)–sulfosalan complexes in aqueous media is presently unknown. For the reaction of Na 2 [Pd(HSS)] ( 6 ) and Na 2 [Pd(BuHSS)] ( 8 ) with H 2 , we obtained evidence of the need for a vacant coordination site for the oxidative addition of H 2 [ 43 , 44 ]. In the present case, the catalytic activity increased with increasing length of the linker chain in the order 6 (14%) < 7 (35%) < 8 (72%).…”

Section: Resultsmentioning

confidence: 99%

“…We have been interested in aqueous organometallic catalysis for several years [ 21 ] and employed as catalysts complexes of transition metals with water-soluble tertiary phosphine and/or N-heterocyclic carbene ligands. Recently, we launched a program to study in aqueous media the catalytic properties of sulfonated salan-based complexes in reactions such as hydrogenation of alkenes and ketones [ 43 ], redox isomerization of allylic alcohols [ 44 , 45 ] and carbon–carbon cross-coupling reactions [ 46 ]. In particular, some Pd (II)–salan complexes were found to be highly effective catalysts for the Sonogashira and the Suzuki–Miyaura cross-coupling reactions [ 46 , 47 ].…”

Section: Introductionmentioning

confidence: 99%

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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

et al. 2020

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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 °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 × 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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Section: Resultsmentioning

confidence: 99%