Reductive Amination of Aldehydes and Amines with an Efficient Pd/NiO Catalyst

Abstract By applying a simple Pd/NiO catalyst, the reductive amination of amines and aldehydes can progress efficiently under mild reaction conditions, and 24 substituted amines with different structures were synthesized with up to 98% isolated yields. GRAPHICAL ABSTRACT

[1]  Yadong Li,et al.  A PdAg bimetallic nanocatalyst for selective reductive amination of nitroarenes. , 2013, Chemical communications.

[2]  Youquan Deng,et al.  Selective Hydrogenation of Nitroaromatic Compounds with a Nickel‐Oxide‐Supported Nano‐Palladium Catalyst under Ambient Reaction Conditions , 2013 .

[3]  A. Corma,et al.  Bifunctional iridium-(2-aminoterephthalate)–Zr-MOF chemoselective catalyst for the synthesis of secondary amines by one-pot three-step cascade reaction ☆ , 2013 .

[4]  R. Shukla,et al.  Rhodium complex encapsulated functionalized hexagonal mesoporous silica for heterogeneous hydroaminomethylation , 2013 .

[5]  M. Beller,et al.  Efficient and regioselective ruthenium-catalyzed hydro-aminomethylation of olefins. , 2013, Journal of the American Chemical Society.

[6]  Thomas J. Colacot,et al.  An examination of the palladium/Mor-DalPhos catalyst system in the context of selective ammonia monoarylation at room temperature. , 2013, Chemistry.

[7]  Zhengping Dong,et al.  Palladium supported on magnetic nanoparticles as recoverable catalyst for one-pot reductive amination of aldehydes with nitroarenes under ambient conditions , 2013 .

[8]  M. Beller,et al.  Copper-catalyzed reductive amination of aromatic and aliphatic ketones with anilines using environmental-friendly molecular hydrogen , 2012 .

[9]  P. Ghorai,et al.  The direct reductive amination of electron-deficient amines with aldehydes: the unique reactivity of the Re2O7 catalyst. , 2012, Chemical communications.

[10]  Zhi‐Xiang Wang,et al.  Catalytic metal-free intramolecular hydroaminations of non-activated aminoalkenes: a computational exploration. , 2012, Dalton transactions.

[11]  C. Claver,et al.  Interplay between cationic and neutral species in the rhodium-catalyzed hydroaminomethylation reaction. , 2012, Chemistry.

[12]  M. D. Mbaye,et al.  Knölker's iron complex: an efficient in situ generated catalyst for reductive amination of alkyl aldehydes and amines. , 2012, Angewandte Chemie.

[13]  M. Beller,et al.  Development of new hydrogenations of imines and benign reductive hydroaminations: zinc triflate as a catalyst. , 2012, ChemSusChem.

[14]  Mayur V. Khedkar,et al.  PS-Pd–NHC: an efficient and heterogeneous recyclable catalyst for direct reductive amination of carbonyl compounds with primary/secondary amines in aqueous medium , 2012 .

[15]  Shichao Yu,et al.  Highly regioselective isomerization-hydroaminomethylation of internal olefins catalyzed by Rh complex with Tetrabi-type phosphorus ligands. , 2012, Organic letters.

[16]  Derek J Schipper,et al.  A catalytic tethering strategy: simple aldehydes catalyze intermolecular alkene hydroaminations. , 2011, Journal of the American Chemical Society.

[17]  M. T. Navarro,et al.  Pt and Pd nanoparticles supported on structured materials as catalysts for the selective reductive amination of carbonyl compounds , 2011 .

[18]  C. Leonelli,et al.  One-pot synthesis of aniline derivatives from nitroarenes under mild conditions promoted by a recyclable polymer-supported palladium catalyst , 2011 .

[19]  Yixiang Cheng,et al.  Direct reductive amination of aromatic aldehydes catalyzed by gold(I) complex under transfer hydrogenation conditions. , 2011, Chemical communications.

[20]  Youquan Deng,et al.  Palladium catalyzed N-alkylation of amines with alcohols , 2011 .

[21]  Youquan Deng,et al.  Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides. , 2011, Chemistry.

[22]  Kangnian Fan,et al.  Efficient and clean gold-catalyzed one-pot selective N-alkylation of amines with alcohols. , 2010, Chemistry.

[23]  N. Ide,et al.  Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine. , 2010, Journal of the American Chemical Society.

[24]  Kaixian Chen,et al.  Ligand-free iron/copper cocatalyzed N-arylations of aryl halides with amines under microwave irradiation , 2010 .

[25]  S. Buchwald,et al.  Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes. , 2009, Angewandte Chemie.

[26]  K. Thurow,et al.  Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies , 2009 .

[27]  B. Sreedhar,et al.  Direct one-pot reductive amination of aldehydes with nitroarenes in a domino fashion: catalysis by gum-acacia-stabilized palladium nanoparticles. , 2009, The Journal of organic chemistry.

[28]  M. Beller,et al.  Hydroaminomethylation with novel rhodium-carbene complexes: an efficient catalytic approach to pharmaceuticals. , 2007, Chemistry.

[29]  Jianguo Mei,et al.  Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings. , 2006, Chemistry.

[30]  S. Buchwald,et al.  Industrial-Scale Palladium-Catalyzed Coupling of Aryl Halides and Amines –A Personal Account , 2006 .

[31]  Shinya Sato,et al.  One-pot reductive amination of aldehydes and ketones with α-picoline-borane in methanol, in water, and in neat conditions , 2004 .

[32]  M. Beller,et al.  Amines made easily: a highly selective hydroaminomethylation of olefins. , 2003, Journal of the American Chemical Society.

[33]  Joop A. Peters,et al.  Preparation of Benzylamine by Highly Selective Reductive Amination of Benzaldehyde Over Ru on an Acidic Activated Carbon Support as the Catalyst , 2002 .

[34]  K. W. Jung,et al.  Synthesis of Secondary Amines , 2001 .

[35]  V. Tarasevich,et al.  Reductive amination of oxygen-containing organic compounds , 1999 .

[36]  B. D. Harris,et al.  Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1). , 1996, The Journal of organic chemistry.

[37]  M. DiMare,et al.  A MILD, PYRIDINE : BORANE-BASED REDUCTIVE AMINATION PROTOCOL , 1995 .

[38]  K. Cowen,et al.  An improved method for reductive alkylation of amines using titanium(IV) isopropoxide and sodium cyanoborohydride , 1990 .