A pyridyl-triazole ligand for ruthenium and iridium catalyzed CC and CO hydrogenations in water/organic solvent biphasic systems

Abstract

a b s t r a c tThe water soluble pyridyl-triazole ligand sodium 2-(1-((pyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl) ethyl sulfate (Na1) has been successfully employed in combination with ruthenium and iridium for catalytic hydrogenation of C C and C O double bonds in water/toluene biphasic systems. Reaction of the ligand with [RuCl 2 ( 6 -p-cymene)] 2 affords the new water soluble complex [RuCl( 6 -p-cymene)(1)] (2) which has been found to be catalytically active in the water/organic solvent biphasic hydrogenation using styrene and 2-cyclohexen-1-one as model substrates. Very conveniently, the iridium based catalytic system is prepared by simply stirring in water [Ir( 4 -COD)Cl] 2 with Na1 (Ir:Na1 molar ratio = 1:4), the resulting solution is catalytically active and appears more efficient than 2. With both the Ru-and Ir-based systems the catalytically active aqueous phases can be used at least three times without loss of activity.

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

“…Our research group has long been involved in the study of innovative sustainable processes for fine chemistry [ 51 , 52 , 53 , 54 ]. Recently, our studies have focused on the development of new dehydro-condensation agents.…”

Synthesis of a water-soluble thio-triazole ligand for biphase rhodium catalyzed hydroformylation of styrene

“…The ligand 1, (2-(1-(2-(methylthio)ethyl)-1H-1,2,3-triazol-4-yl)ethanol) was synthesized as described in the literature method [23]. Duplicate or triplicate hydroformylation reactions were carried out under inert atmosphere using Schlenk techniques [13]. The obtained results generally agreeing within 5%.…”

“…The organometallic complexes containing watersoluble ligands could be the best tool for biphasic systems [11,12]. Besides hydroformylation reaction, several reactions like hydrogenation reactions [13], Suzuki coupling reaction [14] etc. were catalyzed by catalyst containing water soluble ligand.…”

The intriguing methoxycarbonylation of trimethylsilylacetylene in the presence of Drent's catalytic system

“…Owing to the complete atom economy, it represents a sustainable synthetic route to 2‐trimethylsilylacrylates, a family of intriguing intermediates until now accessible only trough multistep synthetic schemes. [ 30 ]…”