Pd-catalyzed aldehyde to ester conversion: a hydrogen transfer approach.

Aliphatic and aromatic aldehydes are successfully converted into their corresponding esters using Pd(OAc)(2) and XPhos. This approach utilizes a hydrogen transfer protocol: concomitant reduction of acetone to isopropanol provides an inexpensive and sustainable approach that mitigates the need for other oxidants.

[1]  Andrew J Boydston,et al.  Organocatalyzed anodic oxidation of aldehydes. , 2012, Journal of the American Chemical Society.

[2]  Dong Liu,et al.  Covalently bound benzyl ligand promotes selective palladium-catalyzed oxidative esterification of aldehydes with alcohols. , 2012, Angewandte Chemie.

[3]  G. Heropoulos,et al.  A clean, palladium-catalyzed oxidative esterification of aldehydes using benzyl chloride , 2011 .

[4]  Guoying Zhang,et al.  Palladium/NHC-catalyzed oxidative esterification of aldehydes with phenols , 2011 .

[5]  Pedro M. P. Gois,et al.  NHC/iron cooperative catalysis: aerobic oxidative esterification of aldehydes with phenols. , 2011, Organic & biomolecular chemistry.

[6]  S. Buchwald,et al.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids. , 2010, Journal of the American Chemical Society.

[7]  S. Grimme,et al.  NHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of amines. , 2010, Journal of the American Chemical Society.

[8]  Brooks E. Maki,et al.  N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters. , 2008, Organic letters.

[9]  Gary A. Molander,et al.  Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation. , 2008, Journal of the American Chemical Society.

[10]  S. Connon,et al.  Nucleophilic carbene-catalysed oxidative esterification reactions , 2008 .

[11]  J. Bäckvall,et al.  Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer--a biomimetic approach. , 2008, Angewandte Chemie.

[12]  W. Su,et al.  Palladium-catalyzed aromatic esterification of aldehydes with organoboronic acids and molecular oxygen. , 2008, Organic letters.

[13]  T. Yokoyama,et al.  [IrCl(cod)]2-catalyzed direct oxidative esterification of aldehydes with alcohols , 2007 .

[14]  Q. Guo,et al.  Pd-catalyzed aerobic oxidative coupling of anilides with olefins through regioselective C–H bond activation , 2007 .

[15]  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.

[16]  C. Wolf,et al.  Bisoxazolidine-catalyzed enantioselective alkynylation of aldehydes. , 2006, Journal of the American Chemical Society.

[17]  J. Bode,et al.  Catalytic generation of activated carboxylates from enals: a product-determining role for the base. , 2005, Organic letters.

[18]  S. Kiyooka,et al.  Iridium-catalyzed oxidative esterification reaction of aliphatic aldehydes and olefinic alcohols with precoordination of the double bond of alcohols to iridium , 2005 .

[19]  T. Onami,et al.  Esterification of Aldehydes and Alcohols with Pyridinium Hydrobromide Perbromide in Water , 2004 .

[20]  D. D. De Vos,et al.  Toward waste-free production of Heck products with a catalytic palladium system under oxygen. , 2003, Angewandte Chemie.

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

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

[23]  J. Bäckvall,et al.  Ruthenium(II)‐Catalyzed Oppenauer‐Type Oxidation of Secondary Alcohols , 1996 .

[24]  H. Grennberg,et al.  Multistep electron transfer in palladium-catalyzed aerobic oxidations via a metal macrocycle-quinone system , 1990 .

[25]  Y. Maeda,et al.  Ruthenium-catalyzed oxidative transformation of alcohols and aldehydes to esters and lactones , 1987 .

[26]  W. Steglich,et al.  Simple Method for the Esterification of Carboxylic Acids , 1978 .

[27]  J. Bäckvall,et al.  Multi-step catalysis for the oxidation of oleftns to ketones by molecular oxygen in chloride free media , 1988 .

[28]  R. Grigg,et al.  Oxidation of alcohols by transition metal complexes—iv : The rhodium catalysed synthesis of esters from aldehydes and alcohols , 1981 .

[29]  Robert S. Shue Catalytic coupling of aromatics and olefins by homogeneous palladium(II) compounds under oxygen , 1971 .