“…A bimetallic Pt-Bi catalyst supported on activated carbon in the presence of hydrogen peroxide has been used, which showed better selectivity (84%), but poor conversion (34%) [9]. Scott et al, utilized metallic and bimetallic nanocrystal as a catalysts in aqueous medium and achieved ~34% conversion [10]. Similarly, Pt or palladium (Pd) catalysts with comparable results have also been utilized [8,[11][12][13].…”
“…A bimetallic Pt-Bi catalyst supported on activated carbon in the presence of hydrogen peroxide has been used, which showed better selectivity (84%), but poor conversion (34%) [9]. Scott et al, utilized metallic and bimetallic nanocrystal as a catalysts in aqueous medium and achieved ~34% conversion [10]. Similarly, Pt or palladium (Pd) catalysts with comparable results have also been utilized [8,[11][12][13].…”
“…[1][2][3] Aqueous reactions are especially important for oxidation processes since reactions that are possibly explosive under oxidation conditions can be avoided. [4][5][6][7] N-Heterocyclic carbenes (NHCs) represent appropriate ligands for aqueous metalcatalyzed oxidation reactions since metal complexes of NHCs show high thermal, air, and moisture stability. [8][9][10] Although water-soluble NHC complexes have been explored as catalysts in a number of C-C coupling reactions, their application as an oxidation catalyst is not previously known.…”
Various imidazolium salts bearing hydrophilic groups were prepared that reacted with copper powder to afford watersoluble copper complexes of N-heterocyclic carbenes. These copper complexes can catalyze the selective oxidation of benzyl alcohols to the corresponding aldehydes in water at room temperature without the need for a base.Transition-metal-catalyzed reactions in an environmentally friendly and inexpensive reaction media is of great importance for both academic research and industrial applications. Water is nonflammable, safe, and inexpensive compared to organic solvents, thus has attracted much attention in organic synthesis. Organic transformations in water make separation of the organic product easier as the product is extracted from the aqueous layer. 1-3 Aqueous reactions are especially important for oxidation processes since reactions that are possibly explosive under oxidation conditions can be avoided. 4-7 N-Heterocyclic carbenes (NHCs) represent appropriate ligands for aqueous metalcatalyzed oxidation reactions since metal complexes of NHCs show high thermal, air, and moisture stability. 8-10 Although water-soluble NHC complexes have been explored as catalysts in a number of C-C coupling reactions, their application as an oxidation catalyst is not previously known. 10Copper is an appropriate reagent for the oxidation of alcohols due to its low cost and low toxicity. 11 We have reported that copper complexes of NHCs can be easily obtained through direct reaction of commercially available copper powder with imidazolium salts. 12 Thus water-soluble copper catalysts would be easily obtained if the imidazolium salts were anchored to hydrophilic groups. As an extension of our organometallic chemistry of functionalized NHCs, 13 here we present a facile and practical method for the aerobic oxidation of benzyl alcohols to the corresponding aldehydes in water at room temperature. The water-soluble copper catalysts are easily in situ generated from copper powder and imidazolium salts bearing hydrophilic groups.
Figure 1 Schematic illustration of water-soluble imidazolium saltsA few imidazolium salts L1-L5 bearing hydrophilic groups were prepared (Figure 1). Imidazolium salts L1 and L2 were obtained by quaternarization of 1-methyl-1H-imidazole and 1-(2-pyridyl)-1H-imidazole with a (bromoalkyl)ammonium bromide in acetonitrile, and they were isolated as hydrophilic solids in 64% and 70% yields. Compound L3 was prepared from the condensation of a 3-(3-bromopropyl)-1-phenyl-1H-imidazol-3-ium compound with an [2-(dimethylamino)ethyl]ammonium bromide. Compound L4 and L5 were prepared from 1-methyl-1H-imidazole and 1-(2-pyridyl)-1H-imidazole with 1,3-propanesultone in acetonitrile in 80% and 62% yields according to known procedures. 14 These salts were characterized by NMR spectroscopy and the characterization data, together with synthetic details, are given in the Supporting Information; all the imidazolium salts are hygroscopic and well soluble in water.
“…(NH 4 ) 2 PdCl 6 dissolved in the aqueous phase was reduced at 45 ° C by the hydroxyl group of the emulsifying agent Triton X-100. Subsequently, HAuCl 4 dissolved in [C 4 C 1 Im] [PF 6 ] was reduced on the surface of the Pd cores, provoking the temporary release of Pd 2 + , which was subsequently reduced yet again on the surface of the NPs [46] . Santini ' s group has also reported the synthesis of bimetallic Ru-Ta NPs using Ru(COD)(COT) and Tris(neopentyl) neopentylidene tantalum(V) (TaNp 3 = Np) as precursors [88] .…”
Section: Synthesis and Characterization Of Bimetallic Nps In Ilsmentioning
confidence: 99%
“…In their ongoing studies about bimetallic Au-Pd NPs in ILs, Scott et al found that these materials are suitable for the oxidation of α , β -unsaturated alcohols (Scheme 5 ) [46] . Besides PVP-stabilized bimetallic particles, the authors evaluated tetraalkylphosphonium chloride ILs as stabilizers during the sequential reduction of the metal precursors yielding a variety of core-shell particles.…”
Section: Oxidationmentioning
confidence: 99%
“…However, only few reports exist on metal oxides and bimetallic alloy or core-shell NPs in ILs, as precursors and/or catalysts for transformations in multiphase systems [13, 32 -55] . Their potential applications cover such fields as hydrogenation reactions [32,33,36,40,45] , hydrogenolysis [39,56] , C-C coupling [41] , C-C bond cleavage [13] , dehalogenation of arenes [55] , condensation reactions [54] , oxidation [46] , as well as electrochemical applications [42, 47, 51 -53, 57, 58] . The scope of the present review is to discuss the mentioned traditional catalytic applications, excluding electrochemical applications.…”
Ionic liquids (ILs) are well established as solvents and stabilizing agents for the synthesis of metallic nanoparticles (NPs) in general. The physicochemical properties of ILs and the supramolecular organization in the liquid state are capable of directing the growth of transition metal NPs generated in situ and to subsequently protect and stabilize them. Until now, many different NPs have been successfully synthesized within these media; however, the synthesis of metal oxide and bimetallic alloy or core-shell NPs in ILs is still relatively rare. Herein, we summarize the current state-of-the-art of the synthetic methods for these materials and their application in the broad field of catalysis, including multiphase systems, hydrogenation, dehydrogenation, functionalization, as well as defunctionalization reactions.
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