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These catalysts have been investigated for industrially important processes like the oxidation of alcohols, oxidation of carbon monoxide CO , and various selective hydrogenation reactions e. Though often efficient and exhibiting useful or unique selectivities, there is considerable uncertainty with respect to the mechanism of processes catalyzed by various heterogeneous gold catalysts, even compared to other heterogeneous transition metal catalysts.
In contrast, homogeneous catalysis with gold uses simple or ligand-bound gold I or gold III compounds that are soluble in organic solvents and is used for the synthesis of fine chemicals in organic chemistry. These gold sources, however, quickly give rise to ill-defined and easily deactivated via reduction to Au 0 active catalysts in solution.
The development of well-defined phosphine- or NHC-ligated gold I complexes was an important advance and led to significant increase in interest in the synthetic applications of gold catalysis. Ligated gold I complexes are typically prepared and stored as the bench-stable but unreactive chlorides, LAuCl, e. Gold is certainly not the only metal showing this type of bonding and reactivity, several metal ions isolobal with the simple proton i.
Gold I -alkene and -alkyne complexes are electrophilic and susceptible toward nucleophilic attack. In oxymercuration the resultant organomercurial species is generated stoichiometrically, and requires an additional step to liberate the product.
In the case of gold, protonolysis of the Au-C bond closes the catalytic cycle, allowing the coordination of another substrate. Some practical advantages of gold I catalysis include: 1 air stability due to the high oxidation potential of Au I , 2 tolerance towards adventitious moisture due its low oxophilicity , and 3 relatively low toxicity compared to other pi-acids e. This particular reaction demonstrated fantastic catalytic efficiency and would trigger a flurry of research into the use of phosphinegold I complexes for the activation C-C multiple bonds in the years to come.
As a consequence of relativistically expanded 5 d orbitals, the LAu fragment can stabilize a neighboring carbocation via electron donation into the empty p -type orbital. Thus, in addition to their expected carbocation-like reactivity, these cations also exhibit significant carbene character, a property that has been exploited in catalytic transformations such as cyclopropanation and C-H insertion.
Although Echavarren first reported the preparation of chiral bisphosphinedigold I complexes for enantioselective gold catalysis proceeding via the typical pi-activation mechanism,  an early, atypical example of enantioselective catalysis by gold was described by Hayashi and Ito in Since oxazolines can be hydrolyzed to provide a 1,2-aminoalcohol, this reaction constitutes the first example of a catalytic, asymmetric aldol reaction.
In contrast to the other reactions described above, this reaction does not involve activation of a C-C double or triple bond by gold. In a simple mechanistic picture, gold I simultaneously coordinates to two phosphine ligands and the carbon isocyanate group  which is then attacked by the carbonyl group. Further studies on the bonding mode of Au I indicate that this simple picture may have to be revised. Heterogeneous gold catalysis is an older science. Gold is an attractive metal to use because of its stability against oxidation and its variety in morphology for instance gold cluster materials.
Gold has been shown to be effective in low-temperature CO oxidation and acetylene hydrochlorination to vinyl chlorides. The exact nature of the catalytic site in this type of process is debated. However, other metals can do the same job inexpensively, notably in recent years iron see organoiron chemistry. Shen summarized homogeneous reactions forming cyclic compounds into 4 main categories: .
Other reactions are the use of gold in C—H bond activation  and aldol reactions. Gold also catalyses coupling reactions. While gold-catalyzed hydrofunctionalization of alkynes, allenes, and allylic alcohols  occurs readily under comparatively mild conditions, unactivated alkene remain poor substrates in most cases,  in large part due to the resistance of the intermediate alkylgold I complexes to protodeauration.
From Wikipedia, the free encyclopedia. For the company, see Organo Gold. Wiley-VCH: Weinheim. Gold Bulletin. Journal of the American Chemical Society. Chemical Society Reviews. ISSN PMID Structures of lithium dimethylaurate and lithium tetramethylaurate in solution". Inorganic Chemistry. Journal of Chemical Education. Bibcode : JChEd.. PMC Dean Accounts of Chemical Research. Organo Gold was born. The rest is history.
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