N-heterocyclic carbene catalyzed oxidative coupling of aldehydes with carbodiimides under aerobic conditions: efficient synthesis of N-acylureas.

The oxidative coupling reaction of aldehydes with N,N'-disubstituted carbodiimides catalyzed by N-heterocyclic carbenes under aerobic conditions has been achieved. This reaction gives the corresponding N-acylurea derivatives in good to high yields. Various kinds of aldehydes including aliphatic ones and carbodiimides are applicable to this reaction.

[1]  Frank Glorius,et al.  Organocatalytic umpolung: N-heterocyclic carbenes and beyond. , 2012, Chemical Society reviews.

[2]  K. Scheidt,et al.  Cooperative Lewis acid/N-heterocyclic carbene catalysis. , 2012, Chemical science.

[3]  M. D’hooghe,et al.  N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis , 2012, Beilstein journal of organic chemistry.

[4]  A. Mann,et al.  Acylthiourea, acylurea, and acylguanidine derivatives with potent hedgehog inhibiting activity. , 2012, Journal of medicinal chemistry.

[5]  D. Enders,et al.  N-heterocyclic carbene catalyzed domino reactions. , 2012, Angewandte Chemie.

[6]  R. Menon,et al.  Employing homoenolates generated by NHC catalysis in carbon-carbon bond-forming reactions: state of the art. , 2011, Chemical Society reviews.

[7]  Sun Min Kim,et al.  NHC-Assisted One-Pot Domino Oxidation of Aldehydes into Carboxylic Acids using Sodium Hydride under Oxygen Atmosphere , 2011 .

[8]  Frank Glorius,et al.  Extending NHC-catalysis: coupling aldehydes with unconventional reaction partners. , 2011, Accounts of chemical research.

[9]  E. Yashima,et al.  Oxidative esterification, thioesterification, and amidation of aldehydes by a two-component organocatalyst system using a chiral N-heterocyclic carbene and redox-active riboflavin. , 2011, Chemistry.

[10]  F. Glorius,et al.  Dual Activation in N-Heterocyclic Carbene-Organocatalysis , 2011 .

[11]  J. Bode,et al.  On the role of CO2 in NHC-catalyzed oxidation of aldehydes. , 2011, Organic letters.

[12]  Xue‐Wei Liu,et al.  N-Heterocyclic carbene-mediated oxidative esterification of aldehydes: ester formation and mechanistic studies. , 2011, The Journal of organic chemistry.

[13]  S. W. Youn,et al.  NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: synthesis of O-heterocycles. , 2011, Organic letters.

[14]  Hogyu Han,et al.  Oxidation of benzoins to benzoic acids using sodium hydride under oxygen atmosphere , 2011 .

[15]  Andrew D. Smith,et al.  α-Aroyloxyaldehydes: scope and limitations as alternatives to α-haloaldehydes for NHC-catalysed redox transformations. , 2011, Chemical communications.

[16]  A. Studer,et al.  NHC-catalyzed Michael addition to α,β-unsaturated aldehydes by redox activation. , 2010, Angewandte Chemie.

[17]  K. Zeitler,et al.  Efficient catalytic, oxidative lactonization for the synthesis of benzodioxepinones using thiazolium-derived carbene catalysts. , 2010, Organic letters.

[18]  F. Glorius,et al.  The measure of all rings--N-heterocyclic carbenes. , 2010, Angewandte Chemie.

[19]  R. Menon,et al.  NHC catalyzed transformation of aromatic aldehydes to acids by carbon dioxide: an unexpected reaction. , 2010, Organic letters.

[20]  A. Studer,et al.  Oxidative amidation and azidation of aldehydes by NHC catalysis. , 2010, Organic letters.

[21]  Yugen Zhang,et al.  Unexpected CO2 splitting reactions to form CO with N-heterocyclic carbenes as organocatalysts and aromatic aldehydes as oxygen acceptors. , 2010, Journal of the American Chemical Society.

[22]  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.

[23]  Yukinori Katagiri,et al.  Oxidative carboxylation of arylaldehydes with water by a sulfoxylalkyl-substituted N-heterocyclic carbene catalyst. , 2009, Organic & biomolecular chemistry.

[24]  Brooks E. Maki,et al.  N-Heterocyclic Carbene-Catalyzed Oxidations. , 2009, Tetrahedron.

[25]  V. Nair,et al.  Recent advances in carbon-carbon bond-forming reactions involving homoenolates generated by NHC catalysis. , 2008, Chemical Society reviews.

[26]  S. Grimme,et al.  Biomimetic carbene-catalyzed oxidations of aldehydes using TEMPO. , 2008, Angewandte Chemie.

[27]  D. Enders,et al.  Lessons from nature: biomimetic organocatalytic carbon-carbon bond formations. , 2008, The Journal of organic chemistry.

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

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

[30]  D. Enders,et al.  Organocatalysis by N-heterocyclic carbenes. , 2007, Chemical reviews.

[31]  Nicolas Marion,et al.  N-heterocyclic carbenes as organocatalysts. , 2007, Angewandte Chemie.

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

[33]  J. Bode,et al.  N-heterocyclic carbene catalyzed C--C bond cleavage in redox esterifications of chiral formylcyclopropanes. , 2006, Angewandte Chemie.

[34]  Yong Wu,et al.  Unexpected ring-opening reactions of aziridines with aldehydes catalyzed by nucleophilic carbenes under aerobic conditions. , 2006, Organic letters.

[35]  K. Zeitler Stereoselective Synthesis of (E)-α,β-Unsaturated Esters via Carbene-Catalyzed Redox Esterification , 2006 .

[36]  K. Zeitler,et al.  Extending mechanistic routes in heterazolium catalysis--promising concepts for versatile synthetic methods. , 2005, Angewandte Chemie.

[37]  T. Rovis,et al.  Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of alpha-chloroesters. , 2005, Journal of the American Chemical Society.

[38]  M. Christmann New developments in the asymmetric Stetter reaction. , 2005, Angewandte Chemie.

[39]  K. Scheidt,et al.  Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes , 2005 .

[40]  A. Córdova,et al.  Direct Amino Acid Catalyzed Asymmetric α Oxidation of Ketones with Molecular Oxygen , 2004 .

[41]  J. Bode,et al.  N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes. , 2004, Journal of the American Chemical Society.

[42]  A. Córdova,et al.  The direct amino acid-catalyzed asymmetric incorporation of molecular oxygen to organic compounds. , 2004, Journal of the American Chemical Society.

[43]  Jeffrey S. Johnson Catalyzed reactions of acyl anion equivalents. , 2004, Angewandte Chemie.

[44]  V. Nair,et al.  Unprecedented reactivity of N-heterocyclic carbenes toward DMAD and aldehydes leading to novel multicomponent reactions. , 2003, Organic letters.

[45]  S. Schenone,et al.  N-Acyl-N-phenyl ureas of piperidine and substituted piperidines endowed with anti-inflammatory and anti-proliferative activities. , 2001, Farmaco.

[46]  P. Tipton,et al.  Evidence for Urate Hydroperoxide as an Intermediate in the Urate Oxidase Reaction , 2000 .

[47]  C. Marsden,et al.  Early Treatment of Parkinson’s Disease with Cabergoline Delays the Onset of Motor Complications , 1998, Drugs.

[48]  C. Adler,et al.  Multicenter, placebo-controlled trial of cabergoline taken once daily in the treatment of Parkinson's disease , 1996, Neurology.

[49]  M. Ślebioda Substituent effect in reaction of dicyclohexylcarbodiimide with substituted benzoic acids , 1995 .

[50]  D. Enders,et al.  Preparation, Structure, and Reactivity of 1,3,4-Triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene, a New Stable Carbene† , 1995 .

[51]  J. Obeso,et al.  Cabergoline in Parkinson's disease , 1993, Neurology.

[52]  P. Gayral,et al.  Synthe`se de cyanace´tylure´es en vue d'essais vis-a`-vis d'Hymenolepis nana , 1989 .

[53]  S. Mantegani,et al.  Synthesis and nidation inhibitory activity of a new class of ergoline derivatives , 1989 .

[54]  A. Igau,et al.  Analogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetylene , 1988 .

[55]  G. Stork,et al.  Conjugate addition of acyl carbanion equivalents via the protected cyanohydrin method , 1974 .

[56]  R. Silverstein,et al.  Reactions of Carbodiimides. I. The Mechanisms of the Reactions of Acetic Acid with Dicyclohexylcarbodiimide1,2 , 1966 .

[57]  貞二 鵜飼,et al.  アチロイン縮合に於ける新觸媒群に就て (第1報) チアツオリウム鹽基或は共核開裂成績體の作用 , 1943 .

[58]  R. Srivastava,et al.  Microwave-mediated and customery synthesis of N-benzoyl- or N-substituted benzoyl-N,N'-dialkylureas from arylcarboxylic acids and N,N'-disubstituted carbodiimides under solvent-free conditions , 2007 .

[59]  Richard L. Harlow,et al.  A stable crystalline carbene , 1991 .

[60]  A. Demilo,et al.  Heterocyclic analogs of diflubenzuron as growth and reproduction inhibitors of the fall armyworm and house fly , 1978 .