Gold catalysis: in situ EXAFS study of homogeneous oxidative esterification.

Gold complexes were prepared and investigated as catalysts for the oxidative esterification of aldehydes. Stabilisation by pyridine ligands gave good conversions and the in situ extended X-ray absorption fine structure (EXAFS) study of the reactions indicated that the reaction mixtures contained only mononuclear gold species. Thus, this is the first proof for a homogeneous gold-catalysed oxidation reaction; the presence of nanoparticles could be excluded experimentally.

[1]  Alois Fürstner,et al.  Katalytische carbophile Aktivierung: Platin‐ und Gold‐π‐Säuren als Katalysatoren , 2007 .

[2]  M. Jansen,et al.  Anionic Gold in Cs3AuO and Rb3AuO Established by X-ray Absorption Spectroscopy , 1995 .

[3]  A. Villa,et al.  Synergetic effect of platinum or palladium on gold catalyst in the selective oxidation of D-sorbitol , 2005 .

[4]  Gianmario Martra,et al.  Metal sols as a useful tool for heterogeneous gold catalyst preparation: reinvestigation of a liquid phase oxidation , 2000 .

[5]  T. Fukuyama,et al.  Mizoroki-Heck arylation of alpha,beta-unsaturated acids with a hybrid fluorous ether, F-626: facile filtrative separation of products and efficient recycling of a reaction medium containing a catalyst. , 2004, The Journal of organic chemistry.

[6]  G. Natile,et al.  Reduction of gold(III) to gold(I) by dialkyl sulphides. Evidence for an atom-transfer redox process , 1980 .

[7]  Liming Zhang,et al.  Gold-catalyzed homogeneous oxidative cross-coupling reactions. , 2009, Angewandte Chemie.

[8]  G. Hutchings,et al.  Oxidation of glycerol using supported Pt, Pd and Au catalysts , 2003 .

[9]  A. Loupy,et al.  Solid-liquid phase-transfer catalysis without solvent: mild and efficient conditions for saponifications and preparations of hindered esters , 1986 .

[10]  P. Gallezot,et al.  Selective oxidation of alcohols and aldehydes on metal catalysts , 2000 .

[11]  A. Echavarren,et al.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective. , 2008, Chemical reviews.

[12]  B. Borhan,et al.  Facile oxidation of aldehydes to acids and esters with Oxone. , 2003, Organic letters.

[13]  Liming Zhang,et al.  Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates. , 2009, Bioorganic & medicinal chemistry letters.

[14]  L. Prati,et al.  Gold on Carbon as a New Catalyst for Selective Liquid Phase Oxidation of Diols , 1998 .

[15]  Y. Venkateswarlu,et al.  A Mild and Efficient Chemoselective Protection of Primary Alcohols as Pivaloyl Esters Using La(NO3)3·6H2O as a Catalyst under Solvent-free Conditions , 2007 .

[16]  B. Karimi,et al.  An improved protocol for aerobic oxidation of acetals to esters catalyzed by N-hydroxy phthalimide (NHPI) and lipophilic Co(II) complexes , 2005 .

[17]  Gopinath,et al.  A catalytic oxidative esterification of aldehydes using V2O5-H2O2 , 2000, Organic letters.

[18]  Brooks E. Maki,et al.  Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes. , 2007, Organic letters.

[19]  S. Buchwald,et al.  A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles. , 2008, Angewandte Chemie.

[20]  F. Porta,et al.  Selective liquid phase oxidation using gold catalysts , 2000 .

[21]  Y. Geletii,et al.  A homogeneous catalyst for selective O(2) oxidation at ambient temperature. diversity-based discovery and mechanistic investigation of thioether oxidation by the Au(III)Cl(2)NO(3)(thioether)/O(2) system. , 2001, Journal of the American Chemical Society.

[22]  M. Beller,et al.  A general gold-catalyzed direct oxidative coupling of non-activated arenes. , 2008, Chemical communications.

[23]  Masatake Haruta,et al.  When gold is not noble: catalysis by nanoparticles. , 2003, Chemical record.

[24]  Zhangjie Shi,et al.  Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water. , 2006, Organic letters.

[25]  L. Prati,et al.  Gold catalyzed oxidation of aldehydes in liquid phase , 2003 .

[26]  L. Prati,et al.  New gold catalysts for liquid phase oxidation , 1999 .

[27]  O. Lohse.  The Palladium Catalysed Suzuki Coupling of 2- and 4-Chloropyridines , 1999 .

[28]  L. Prati,et al.  Selective oxidation using gold. , 2008, Chemical Society reviews.

[29]  M. Neuburger,et al.  A new gold-catalyzed domino cyclization and oxidative coupling reaction. , 2008, Chemistry.

[30]  A. Robertson,et al.  Efficient carbonylation reactions in phosphonium salt ionic liquids: anionic effects. , 2007, Organic letters.

[31]  F. d’Acapito,et al.  Determination of the oxidation and coordination state of copper on different Cu-based catalysts by XANES spectroscopy in situ or in operando conditionsPresented at the International Congress on Operando Spectroscopy, Lunteren, The Netherlands, March 2?6, 2003. , 2003 .

[32]  J. Kenyon,et al.  XIII.—Investigations on the dependence of rotatory power on chemical constitution. Part XII. The rotatory powers of some esters of benzoic and of 1- and 2-naphthoic acids with optically active secondary alcohols , 1915 .

[33]  A. Corma,et al.  A collaborative effect between gold and a support induces the selective oxidation of alcohols. , 2005, Angewandte Chemie.

[34]  A new manifold for the Morita reaction: diene synthesis from simple aldehydes and acrylates/acrylonitrile mediated by phosphines. , 2007, Chemical communications.

[35]  A Stephen K Hashmi,et al.  Gold-catalyzed organic reactions. , 2007, Chemical reviews.

[36]  H. Sharghi,et al.  Al2O3/MeSO3H (AMA) as a new reagent with high selective ability for monoesterification of diols , 2003 .

[37]  Alois Fürstner,et al.  Catalytic carbophilic activation: catalysis by platinum and gold pi acids. , 2007, Angewandte Chemie.

[38]  Huanrong Li,et al.  Aerobic oxidation of alcohol in aqueous solution catalyzed by gold , 2007 .

[39]  Comparison of decanethiolate gold nanoparticles synthesized by one-phase and two-phase methods. , 2006, The journal of physical chemistry. B.

[40]  G. Hutchings,et al.  Solvent-free Oxidation of Primary Alcohols to Aldehydes using Supported Gold Catalysts , 2005 .

[41]  H. Neumann,et al.  Efficient Carbonylation of Aryl and Heteroaryl Bromides using a Palladium/Diadamantylbutylphosphine Catalyst , 2006 .

[42]  P. Fristrup,et al.  Mechanistic investigation of the gold-catalyzed aerobic oxidation of aldehydes: added insight from Hammett studies and isotopic labelling experiments. , 2008, Chemical communications.

[43]  K. Mashima,et al.  Transesterification of various methyl esters under mild conditions catalyzed by tetranuclear zinc cluster. , 2008, The Journal of organic chemistry.

[44]  G. M. Smith.  ADDITION COMPOUNDS OF GOLD HALIDES WITH BENZYL SULFIDE , 1922 .

[45]  V. Nair,et al.  Practical synthesis of triaryl- and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride. , 2005, Organic letters.

[46]  Zigang Li,et al.  Gold-catalyzed organic transformations. , 2008, Chemical reviews.

[47]  A. Arcadi.  Alternative synthetic methods through new developments in catalysis by gold. , 2008, Chemical reviews.

[48]  C. Wolf,et al.  Chemoselective nucleophilic arylation and single-step oxidative esterification of aldehydes using siloxanes and a palladium-phosphinous acid as a reaction switch. , 2006, Journal of the American Chemical Society.

[49]  G. Hutchings,et al.  Selective oxidation of glycerol to glyceric acid using a gold catalyst in aqueous sodium hydroxide. , 2002, Chemical communications.

[50]  C. Christensen,et al.  Direct aerobic oxidation of primary alcohols to methyl esters catalyzed by a heterogeneous gold catalyst , 2007 .

[51]  Abraham Nudelman,et al.  NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities. , 1997, The Journal of organic chemistry.

[52]  Zhangjie Shi,et al.  Highly selective aerobic oxidation of alcohol catalyzed by a gold(I) complex with an anionic ligand. , 2005, Journal of the American Chemical Society.

[53]  Hiroki Iida,et al.  Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins. , 2005, Journal of the American Chemical Society.

[54]  Yu Yuan,et al.  Gold(III) catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide , 2007 .

[55]  C. So,et al.  A new family of tunable indolylphosphine ligands by one-pot assembly and their applications in Suzuki-Miyaura coupling of aryl chlorides. , 2008, The Journal of organic chemistry.

[56]  G. Hutchings,et al.  Solvent-Free Oxidation of Primary Alcohols to Aldehydes Using Au-Pd/TiO2 Catalysts , 2006, Science.

[57]  Chao‐Jun Li,et al.  Copper-catalyzed oxidative esterification of alcohols with aldehydes activated by Lewis acids , 2007 .

[58]  A. Corma,et al.  Efficient chemoselective alcohol oxidation using oxygen as oxidant. Superior performance of gold over palladium catalysts , 2006 .