Sodium Hydride Catalyzed Tishchenko Reaction

A convenient and practical method for the dimerization of aldehydes is described. The conversion of aromatic and even heteroaromatic aldehydes in the presence of catalytic amounts of sodium hydride leads to the corresponding Tishchenko esters in high yields (up to 95 %). The reaction can be performed under standard laboratory conditions and on a multigram scale (up to 10 g).

[1]  M. Simon,et al.  An in situ Generated Ruthenium Catalyst for the Tishchenko Reaction , 2010 .

[2]  T. Fukuyama,et al.  Hydroruthenation triggered catalytic conversion of dialdehydes and keto aldehydes to lactones. , 2009, Chemical communications.

[3]  T. Werner.  Phosphonium Salt Organocatalysis , 2009 .

[4]  Daniel C Waddell,et al.  An environmentally benign solvent-free Tishchenko reaction , 2009 .

[5]  C. Wolf,et al.  One-pot oxidative esterification and amidation of aldehydes. , 2008, Chemistry.

[6]  G. Deacon,et al.  Lanthanide formamidinates as improved catalysts for the Tishchenko reaction , 2008 .

[7]  Cheng-Han Hsieh,et al.  Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation , 2007 .

[8]  A. Barrett,et al.  Heavier alkaline Earth amides as catalysts for the Tischenko reaction. , 2007, Organic letters.

[9]  M. Onaka,et al.  The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis , 2006 .

[10]  T. Katoh,et al.  Tishchenko Reaction Using an Iridium-Ligand Bifunctional Catalyst , 2005 .

[11]  Ying-Chieh Wong,et al.  Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride , 2004 .

[12]  Miguel A. Esteruelas,et al.  Reactions of a Hexahydride-Osmium Complex with Aldehydes: Double C−Hα Activation−Decarbonylation and Single C−Hα Activation−Hydroxylation Tandem Processes and Catalytic Tishchenko Reactions , 2004 .

[13]  R. Mahrwald.  The Aldol-Tishchenko Reaction: A Tool in Stereoselective Synthesis , 2003 .

[14]  K. Maruoka,et al.  Isopropoxyaluminum 1,1′-biphenyl-2-oxy-2′-perfluorooctanesulfonamide as a catalyst for Tishchenko reaction , 2003 .

[15]  V. Nevalainen,et al.  Symmetric esters by Tischtschenko reaction of aldehydes catalyzed by bi- and tridentate catalysts derived from catechol or gallol, trimethylaluminum and isopropanol , 2001 .

[16]  P. Roesky,et al.  Homoleptic lanthanide amides as homogeneous catalysts for alkyne hydroamination and the Tishchenko reaction. , 2001, Chemistry.

[17]  G. Deacon,et al.  Simple syntheses, structural diversity, and Tishchenko reaction catalysis of neutral homoleptic rare earth(II or III) 3,5-di-tert-butylpyrazolates--the structures of. , 2001, Chemistry.

[18]  K. Maruoka,et al.  Catalytic, high-speed tishchenko reaction using (2,7-dimethyl-1,8-biphenylenedioxy)bis(diisopropoxyaluminum) as a powerful bidentate catalyst , 1999 .

[19]  P. Roesky,et al.  Homoleptische Lanthanoidamide als Homogenkatalysatoren für die Tischtschenko-Reaktion , 1998 .

[20]  T. Sakakura,et al.  Lanthanoid-catalysed Tishchenko reaction of mono- or di-aldehydes , 1996 .

[21]  Y. Ishii,et al.  Selective dimerization of aldehydes to esters catalyzed by zirconocene and hafnocene complexes , 1993 .

[22]  T. Ohishi,et al.  Dimerization of aldehydes to carboxylic esters catalyzed by K2[Fe(CO)4]–crown ether system , 1993 .

[23]  Y. Koshiro,et al.  Selective Dimerization of Aldehydes to Esters Catalyzed by Hydridoruthenium Complexes , 1982 .

[24]  H. W. Pinnick,et al.  Benzaldehyde plus potassium hydride-benzoyl anion , 1981 .

[25]  Takashi Ito,et al.  A NEW TISHCHENKO-TYPE ESTER FORMATION CATALYZED BY RUTHENIUM COMPLEXES , 1978 .

[26]  Yoshihisa Watanabe,et al.  The Reaction of Disodium Tetracarbonylferrate(–II) with Aldehydes , 1976 .

[27]  P. Stapp.  Boric acid catalyzed Tishchenko reactions , 1973 .

[28]  A. Kawasaki,et al.  Alkoxide transfer from aluminium alkoxide to aldehyde in the Tishchenko reaction , 1969 .

[29]  A. Kawasaki,et al.  Kinetics of the tischenko reaction of acetaldehyde with aluminium isopropoxide , 1967 .

[30]  G. Lewis.  The Reaction of Sodium Hydride with p-Nitrobenzaldehyde , 1965 .

[31]  A. Day,et al.  A Study of the Mixed Tischtschenko Reaction , 1952 .

[32]  F. Nord,et al.  Essential Steps in the Catalytic Condensation of Carbonyl Compounds. III. The Action of Metallic Alkoxides1 , 1947 .

[33]  C. Hauser,et al.  The Action of Sodium Hydride on Certain Carbonyl Compounds. Condensations1 and Reductions , 1946 .

[34]  H. Adkins,et al.  THE CONDENSATION OF ALDEHYDES TO ESTERS BY ALKOXIDES1 , 1925 .

[35]  L. Claisen.  Ueber die Einwirkung von Natriumalkylaten auf Benzaldehyd , 1887 .