67215-70-7Relevant academic research and scientific papers
Enhanced luminescent properties of an open-shell (3,5-Dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl radical by coordination to gold
Hattori, Yohei,Kusamoto, Tetsuro,Nishihara, Hiroshi
, p. 3731 - 3734 (2015)
A gold(I) complex containing an open-shell luminescent (3,5-dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl (PyBTM) radical was prepared. The complex showed fluorescence centered mainly on the coordinated PyBTM ligand. The photophysical and photochemical properties were positively modulated upon coordination to AuI; the photoluminescence quantum yield, fluorescence wavelength, and the stability in the photoexcited state all increased. A gold(I) complex containing an open-shell luminescent (3,5-dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl (PyBTM) radical was prepared. The complex has fluorescence that is centered mainly on the coordinated PyBTM ligand. The photoluminescence quantum yield, fluorescence wavelength, and the stability in the photoexcited state all increased upon coordination to AuI.
Gold(i) compounds with lansoprazole-type ligands: Synthesis, characterization and anticancer properties in vitro
Serratice,Bertrand,Janssen,Hemelt,Zucca,Cocco,Cinellu,Casini
, p. 1418 - 1422 (2014)
A number of gold(i) complexes containing the proton pump inhibitor (PPI) lansoprazole and its reduced precursor 2-((3-methyl-4-(2,2,2-trifluoroethoxy) pyridin-2-yl)methylthio)-1H-benzo[d]imidazole have been synthesized and their biological effects have been evaluated in human cancer and non-tumorigenic cells in vitro. The lansoprazole-based compounds appear to act through a V-H +-ATPase-mediated mechanism.
Pentannulation Reaction by Tandem Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization of Enynyl Vinyl Ethers
Rinaldi, Antonia,Petrovi?, Martina,Magnolfi, Stefano,Scarpi, Dina,Occhiato, Ernesto G.
, p. 4713 - 4717 (2018/08/09)
The tandem gold(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization of propargyl vinyl ether derivatives, followed by in situ reduction of the resulting carbonyl group, provides functionalized cyclopentadienes fused with various N-hetero- and
Silica-Supported Cationic Gold(I) Complexes as Heterogeneous Catalysts for Regio- and Enantioselective Lactonization Reactions
Shu, Xing-Zhong,Nguyen, Son C.,He, Ying,Oba, Fadekemi,Zhang, Qiao,Canlas, Christian,Somorjai, Gabor A.,Alivisatos, A. Paul,Toste, F. Dean
supporting information, p. 7083 - 7086 (2015/06/25)
An efficient method for the synthesis of heterogeneous gold catalysts has been developed. These catalysts were easily assembled from readily available silica materials and gold complexes. The heterogeneous catalysts exhibited superior reactivity in various reactions where protodeauration is the rate-limiting step. Dramatic enhancement in regio- and enantioselectivity was observed when compared to the homogeneous unsupported gold catalyst. The catalysts are easily recovered and recycled up to 11 times without loss of enantioselectivity.
Alkyne/alkene/allene-induced disproportionation of cationic gold(i) catalyst
Kumar, Manish,Jasinski, Jacek,Hammond, Gerald B.,Xu, Bo
supporting information, p. 3113 - 3119 (2014/03/21)
The first detailed experimental study of the deactivation of cationic gold was conducted, and the influence of each component in the reaction system (substrate, counterion, solvent) on the decay process was examined. It was found that a substrate (alkyne/allene/alkene)-induced disproportionation of gold(I) may play a key role in the decay process. Our mechanism is supported by kinetic, XPS, voltammetry studies, and high-resolution ESI-MS data. The first detailed experimental study of the deactivation of cationic gold was conducted, and the influence of each component in the reaction system (substrate, counterion, solvent) on the decay process was examined. It was found that a substrate (alkyne/allene/alkene)-induced disproportionation of gold(I) may play a key role in the decay process (see scheme; TFa=atrifluoromethanesulfonyl).
Auration of the sulfones MeSO2CH2CN and CH 2 (CH2SO2)2CH2
Djordjevic, Bratislav,Schuster, Oliver,Schmidbaur, Hubert
, p. 169 - 174 (2007/10/03)
MeSO2CH2CN shows considerable C-H acidity at its methylene group. Through lithiation followed by reaction with (Ph 3P)AuCl it can therefore be readily converted into the dinuclear, geminally substituted product MeSO2C[Au(PPh3)] 2CN. With an excess of aurating reagents, a third [(Ph 3P)Au] group becomes N-bonded to the nitrile unit to give an ionic trinuclear compound {MeSO2C[Au(PPh3)] 2CNAu(PPh3)}+BF4-. The same product is obtained by direct reaction of MeSO2CH2CN with [(Ph3P)Au]BF4. The crystal structures of the two products have been determined. The diaurated sulfone parts of the molecule and the cation are virtually superimposible. Small Au-C-Au angles and short Au-Au contacts suggest significant aurophilic interactions ("A-frame" structures). The small -C≡N-Au angle of 165.6(5)° in the cation indicates that the strong [(Ph3P)Au]+ acceptor causes substantial changes in the bonding of the nitrile group. Dilithiation of 1,3-dithiane-S,S′-tetroxide followed by reaction with 2 equivalents of (Ph3P)AuCl affords the geminally diaurated compound CH 2(CH2SO2)2C[Au(PPh 3)]2.
Dinuclear Gold(I) "A-Frame" Complexes from Geminal Diauration of 2,4-Diketones, Methylenedisulfones, and Cyanomethyl Sulfones
Djordjevic, Bratislav,Porter, Keith A.,Nogai, Stefan,Schier, Annette,Schmidbaur, Hubert
, p. 5336 - 5344 (2008/10/09)
Treatment of the disulfones RSO2CH2SO2R (R = Me, Ph) with 1 or 2 equiv of organolithium reagents, followed by metathesis with a (phosphine/arsine)gold(I) halide, afforded high yields of mono- or diaurated sulfones of the types [(R′3P)Au]CH(SO 2R)2 (R = R′ = Ph) and [(R′ 3P/As)Au]2{u-C(SO2R)2} (R = Me, R′3P = Ph3P, Ph2MeP, Ph3As; R = Ph, R′3P = PPh3, Ph2MeP). Using the same procedure, PhSO2CH2CN was transformed into [(Ph 3P)Au]2{u-C(CN)SO2Ph}. The products are stable to air and moisture and decompose at temperatures well above 150 °. The crystal structure analysis of the diaurated compounds reveals compact A-frame core units in which the central carbon atom forms a CAu2 triangle with an exceedingly small Au-C-Au angle and, consequently, a short aurophilic Au- - -Au contact. The corresponding angles S-C-S (or SAuC(N)) are widened in an overall distorted-tetrahedral environment. Attempted triauration using [(R′3P)Au]+BF4- reagents was unsuccessful with the disulfones but gave the adduct {[(Ph3P)Au] 2C(SO2Ph)CN[Au(PPh3)]}+BF 4-, in which the third gold atom is attached to the nitrile nitrogen atom. Benzyl phenyl sulfone was monoaurated to give the chiral product [(Ph3P)Au]CH(Ph)SO2Ph. 3-[(Triphenylphosphine)gold]pentane-2,4-dione was found to undergo a redistribution reaction induced by tritert-butoxyaluminum in benzene solution to give the diaurated diketone [(Ph3P)Au] 2{u-C{C(O)Me}2]. Its crystal structure shows a core unit with bonding characteristics similar to those of keto instead of sulfone/cyano substituents.
Gold clustering at Dimethylsulfoximine Me2S(O)NH
Hamel, Armin,Hollatz, Christian,Schier, Annette,Schmidbaur, Hubert
, p. 889 - 894 (2007/10/03)
Polyaurated complexes of the dimethylsulfoximide anion [Me2S(O)N]- have been prepared by reacting N-trimethylsilyl-dimethylsulfoximide with [(Ph3P)Au]BF4 in various molar ratios. With one or two equivalents of t
Polynuclear Gold(I) Complexes of Mercaptocarboxylic Acids
Sladek, Alexander,Schneider, Wolfgang,Angermaier, Klaus,Bauer, Andreas,Schmidbaur, Hubert
, p. 765 - 772 (2007/10/03)
In a search for air-stable and water-soluble mercapto compounds of gold with a high gold content, benzylthiol, α-mercapto-acetic acid, β-mercapto-propionic acid, and thiosalicylic acid were converted into aurated sulfonium salts by treatment with reagents of the type [(R3P)Au]3O+ BF4- or [(R3P)Au]+ BF4-. - BzSH served as a mono-functional model thiol, which was converted into BzS[Au(PMe3)]2+ BF4- (1). The small tertiary phosphine was chosen in order to minimize steric effects. In the crystal the cations are associated into centrosymmetrical climers through short Au-Au contacts (auriophilicity). - The two carboxylic acids with thiol functions, HSCH2COOH and HSCH2CH2COOH, gave triply aurated species of the type {[(Ph3P)Au]2S(CH2)nCOOAu(PPh 3)}+ BF4- (2: n = 2, 3: n = 3). The crystal structure analysis of the representative compound 2 showed again the presence of centrosymmetrical cation dimers with geometrical details of the sulfonium part of the molecules very similar to those of the reference compound 1. In addition, the carboxyl groups in 2 and 3 bear a (phosphine)gold unit mono-hapto bound at one of the oxygen atoms. - 2-HS-C6H4-COOH was converted into a sulfonium salt {[(Ph3P)Au]2S-C6H4-COOH}+ BF4- (4), which crystallizes free of solvent from dry dichloromethane, and as a monohydrate with one mole of dichloromethane (4a = 4·H2O·CH2Cl2) from hydrous CH2Cl2. In the solvent-free crystalline phase (4) the cations are associated into dimers with the usual intermolecular double Au-Au contacts, but in 4a there are monomeric cations with the water molecule hydrogen-bonded to the carboxylic acid function.
