Azobisisobutyronitrile initiated aerobic oxidative transformation of amines: coupling of primary amines and cyanation of tertiary amines.

In the presence of a catalytic amount of radical initiator AIBN, primary amines are oxidatively coupled to imines and tertiary amines are cyanated to α-aminonitriles. These "metal-free" aerobic oxidative coupling reactions may find applications in a wide range of "green" oxidation chemistry.

[1]  H. Miyamura,et al.  Discovery of a metalloenzyme-like cooperative catalytic system of metal nanoclusters and catechol derivatives for the aerobic oxidation of amines. , 2012, Journal of the American Chemical Society.

[2]  Z. Lai,et al.  Enhanced Reactivities toward Amines by Introducing an Imine Arm to the Pincer Ligand: Direct Coupling of Two Amines To Form an Imine Without Oxidant , 2012 .

[3]  Hongbing Ji,et al.  Mimicking the environment of living organisms to achieve the oxidative coupling of amines to imines catalyzed by water-soluble metalloporphyrins , 2012 .

[4]  M. Largeron,et al.  A biologically inspired Cu(I)/topaquinone-like co-catalytic system for the highly atom-economical aerobic oxidation of primary amines to imines. , 2012, Angewandte Chemie.

[5]  Alison E Wendlandt,et al.  Chemoselective organocatalytic aerobic oxidation of primary amines to secondary imines. , 2012, Organic letters.

[6]  E. Alexanian,et al.  Metal-free, aerobic ketooxygenation of alkenes using hydroxamic acids , 2012 .

[7]  Kangnian Fan,et al.  Graphite oxide as an efficient and durable metal-free catalyst for aerobic oxidative coupling of amines to imines , 2012 .

[8]  David C. Fabry,et al.  Light-mediated heterogeneous cross dehydrogenative coupling reactions: metal oxides as efficient, recyclable, photoredox catalysts in C-C bond-forming reactions. , 2012, Chemistry.

[9]  M. Klussmann,et al.  A comparative mechanistic study of Cu-catalyzed oxidative coupling reactions with N-phenyltetrahydroisoquinoline. , 2012, Journal of the American Chemical Society.

[10]  Chuncheng Chen,et al.  Visible-light-induced selective photocatalytic aerobic oxidation of amines into imines on TiO2. , 2012, Chemistry.

[11]  Francesca M. Kerton,et al.  Simple copper/TEMPO catalyzed aerobic dehydrogenation of benzylic amines and anilines. , 2012, Organic & biomolecular chemistry.

[12]  K. R. Prabhu,et al.  C-H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition. , 2012, Organic & biomolecular chemistry.

[13]  K. Loh,et al.  Graphene oxide and Rose Bengal: oxidative C–H functionalisation of tertiary amines using visible light , 2011 .

[14]  Magnus Rueping,et al.  Visible-light photoredox catalyzed oxidative Strecker reaction. , 2011, Chemical communications.

[15]  G. Hutchings,et al.  Low-temperature aerobic oxidation of decane using an oxygen-free radical initiator , 2011 .

[16]  C. Che,et al.  Iron oligopyridine complexes as efficient catalysts for practical oxidation of arenes, alkanes, tertiary amines and N-acyl cyclic amines with Oxone , 2011 .

[17]  Chunhua Yan,et al.  Metal-free aerobic oxidative coupling of amines to imines. , 2011, Chemical communications.

[18]  Tsunehiro Tanaka,et al.  Selective Amine Oxidation Using Nb2O5 Photocatalyst and O2 , 2011 .

[19]  E. Alexanian,et al.  Metal-free, aerobic dioxygenation of alkenes using simple hydroxamic acid derivatives. , 2011, Journal of the American Chemical Society.

[20]  Sanny Verma,et al.  Starch Immobilized Ruthenium Trichloride Catalyzed Oxidative Cyanation of Tertiary Amines with Hydrogen Peroxide. , 2011 .

[21]  Durga Prasad Hari,et al.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation. , 2011, Organic letters.

[22]  R. Patil,et al.  Copper‐Catalyzed Aerobic Oxidation of Amines to Imines under Neat Conditions with Low Catalyst Loading , 2011 .

[23]  Chuncheng Chen,et al.  Selective formation of imines by aerobic photocatalytic oxidation of amines on TiO2. , 2011, Angewandte Chemie.

[24]  Sanny Verma,et al.  Acetone Cyanohydrin: A Convenient Alternative of Toxic Sodium Cyanide/Acetic Acid for Oxidative Cyanation of Tertiary Amines , 2011 .

[25]  M. Albrecht,et al.  Oxidations and Oxidative Couplings Catalyzed by Triazolylidene Ruthenium Complexes , 2011 .

[26]  C. Che,et al.  Silica‐Supported Gold Nanoparticles Catalyzed One‐Pot, Tandem Aerobic Oxidative Cyclization Reaction for Nitrogen‐Containing Polyheterocyclic Compounds , 2011 .

[27]  Yixiang Cheng,et al.  Gold-complexes catalyzed oxidative α-cyanation of tertiary amines. , 2011, Chemical communications.

[28]  M. Antonietti,et al.  Aerobic oxidative coupling of amines by carbon nitride photocatalysis with visible light. , 2011, Angewandte Chemie.

[29]  T. Lambert,et al.  Tropylium ion mediated α-cyanation of amines. , 2011, Journal of the American Chemical Society.

[30]  H. García,et al.  Aerobic Oxidation of Benzyl Amines to Benzyl Imines Catalyzed by Metal–Organic Framework Solids , 2010 .

[31]  Chunbao Li,et al.  Convenient and clean synthesis of imines from primary benzylamines. , 2010, Organic & biomolecular chemistry.

[32]  M. Klussmann,et al.  Autoxidative carbon-carbon bond formation from carbon-hydrogen bonds. , 2010, Angewandte Chemie.

[33]  E. Alexanian,et al.  Metal-free, aerobic dioxygenation of alkenes using hydroxamic acids. , 2010, Angewandte Chemie.

[34]  B. Sain,et al.  Heterogeneously Catalyzed Oxidative Cyanation of Tertiary Amines with Sodium Cyanide/Hydrogen Peroxide using Polymer‐Supported Iron(II) Phthalocyanines as Catalyst , 2010 .

[35]  J. Yoshida,et al.  Direct conversion of benzylamines to imines via atmospheric oxidation in the presence of VO(Hhpic)2 catalyst , 2010 .

[36]  K. I. Goldberg,et al.  Insertion of molecular oxygen into a palladium(II) methyl bond: a radical chain mechanism involving palladium(III) intermediates. , 2009, Journal of the American Chemical Society.

[37]  C. Che,et al.  Graphite-supported gold nanoparticles as efficient catalyst for aerobic oxidation of benzylic amines to imines and N-substituted 1,2,3,4-tetrahydroisoquinolines to amides: synthetic applications and mechanistic study. , 2009, Chemistry, an Asian journal.

[38]  Xue-Yuan Liu,et al.  Selective functionalization of sp(3) C-H bonds adjacent to nitrogen using (diacetoxyiodo)benzene (DIB). , 2009, The Journal of organic chemistry.

[39]  A. Baiker,et al.  Magnetically Separable Gold Catalyst for the Aerobic Oxidation of Amines , 2009 .

[40]  A. Baiker,et al.  A simple preparation of an efficient heterogeneous gold catalyst for aerobic amine oxidation , 2009 .

[41]  A. Ofial,et al.  Iron catalyzed oxidative cyanation of tertiary amines. , 2009, Chemical communications.

[42]  Y. Ishii,et al.  Baeyer–Villiger Oxidation of Cycloalkanones with In Situ Generated Hydrogen Peroxide from Alcohols and Molecular Oxygen Using NHPI as a Key Catalyst , 2009 .

[43]  A. Corma,et al.  Highly active and selective gold catalysts for the aerobic oxidative condensation of benzylamines to imines and one-pot, two-step synthesis of secondary benzylamines , 2009 .

[44]  B. Sain,et al.  An efficient aerobic oxidative cyanation of tertiary amines with sodium cyanide using vanadium based systems as catalysts. , 2009, Chemical communications.

[45]  K. I. Goldberg,et al.  Autoxidation of platinum(IV) hydrocarbyl hydride complexes to form platinum(IV) hydrocarbyl hydroperoxide complexes. , 2009, Inorganic chemistry.

[46]  Chan Woo Lee,et al.  Effective dehydrogenative oxidation of amines and alcohols via radical mechanism by nano-porous polyaniline catalysis , 2009 .

[47]  B. Trewyn,et al.  Aerobic oxidation of amines to imines catalyzed by bulk gold powder and by alumina-supported gold , 2008 .

[48]  T. Nakae,et al.  Ruthenium-catalyzed oxidative cyanation of tertiary amines with molecular oxygen or hydrogen peroxide and sodium cyanide: sp3 C-H bond activation and carbon-carbon bond formation. , 2008, Journal of the American Chemical Society.

[49]  S. Murahashi,et al.  Ruthenium catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450. , 2008, Chemical Society reviews.

[50]  Y. Ishii,et al.  Selective one-pot synthesis of various phenols from diarylethanes. , 2008, Chemical communications.

[51]  A. Chiaroni,et al.  Environmentally friendly chemoselective oxidation of primary aliphatic amines by using a biomimetic electrocatalytic system. , 2008, Chemistry.

[52]  Shainaz M. Landge,et al.  Microwave-assisted oxidative coupling of amines to imines on solid acid catalysts , 2007 .

[53]  Bolin Zhu,et al.  Non-nanogold catalyzed aerobic oxidation of secondary amines to imines. , 2007, Chemical communications.

[54]  Zhangjie Shi,et al.  Multiple deprotonations and deaminations of phenethylamines to synthesize pyrroles. , 2006, Journal of the American Chemical Society.

[55]  A. Chiaroni,et al.  Electrochemically induced cascade reaction for the assembly of libraries of biologically relevant 1,4-benzoxazine derivatives. , 2006, The Journal of organic chemistry.

[56]  S. Sakaguchi,et al.  Aerobic oxidation of 1,3,5-triisopropylbenzene using N-hydroxyphthalimide (NHPI) as key catalyst , 2005 .

[57]  S. Murahashi,et al.  Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide. , 2005, Angewandte Chemie.

[58]  Chao‐Jun Li,et al.  Highly Efficient CuBr-Catalyzed Cross-Dehydrogenative Coupling (CDC) between Tetrahydroisoquinolines and Activated Methylene Compounds , 2005 .

[59]  S. Sakaguchi,et al.  One-pot synthesis of phenol and cyclohexanone from cyclohexylbenzene catalyzed by N-hydroxyphthalimide (NHPI) , 2005 .

[60]  J. Bäckvall,et al.  Efficient ruthenium-catalyzed aerobic oxidation of amines by using a biomimetic coupled catalytic system. , 2005, Chemistry.

[61]  M. North Oxidative Synthesis of α‐Amino Nitriles from Tertiary Amines , 2004 .

[62]  S. Sakaguchi,et al.  Synthesis of Naphthalenediols by Aerobic Oxidation of Diisopropylnaphthalenes Catalyzed by N-Hydroxyphthalimide (NHPI)/α,α′-Azobisisobutyronitrile (AIBN) , 2004 .

[63]  M. Mure Tyrosine-derived quinone cofactors. , 2004, Accounts of chemical research.

[64]  T. Nakae,et al.  Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide. , 2003, Journal of the American Chemical Society.

[65]  M. Largeron,et al.  Oxidation of unactivated primary aliphatic amines catalyzed by an electrogenerated 3,4-azaquinone species: a small-molecule mimic of amine oxidases. , 2003, Angewandte Chemie.

[66]  S. Sakaguchi,et al.  A new strategy for catalytic Baeyer–Villiger oxidation of KA-oil with molecular oxygen using N-hydroxyphthalimide , 2001 .

[67]  D. Enders,et al.  Some recent applications of a-amino nitrile chemistry , 2000 .

[68]  T. Hirao,et al.  An Organic Catalytic System for Dehydrogenative Oxidation. , 1998, The Journal of organic chemistry.

[69]  Joseph P. Adams Imines, enamines and oximes , 2010 .

[70]  G. Dyker Amino Acid Derivatives by Multicomponent Reactions , 1997 .

[71]  K. Kishore,et al.  High-pressure kinetics of vinyl polyperoxides , 1996 .

[72]  S. Murahashi Synthetic Aspects of Metal‐Catalyzed Oxidations of Amines and Related Reactions , 1995 .

[73]  Y. Ishii,et al.  Oxidation of Benzylic Derivatives with Dioxygen Catalyzed by Mixed Addenda Metallophosphate Containing Vanadium and Molybdenum , 1993 .

[74]  Jianhua Ren,et al.  Synthesis of sterically hindered imines , 1993 .

[75]  E. Janzen,et al.  Detection of alkyl, alkoxyl, and alkyperoxyl radicals from the thermolysis of azobis(isobutyronitrile) by ESR/spin trapping. Evidence for double spin adducts from liquid-phase chromatography and mass spectroscopy , 1990 .

[76]  A. Sopchik,et al.  Stereo- and regiochemistries of the oxidations of 2-methoxy-5-tert-butyl-1,3,2-dioxaphosphorinanes and the cyclic methyl 3',5'-phosphite of thymidine by water/iodine and oxygen/AIBN to P-chiral phosphates. Oxygen-17 NMR assignment of phosphorus configuration to the diastereomeric thymidine cyclic me , 1989 .

[77]  N. Porter Mechanisms for the autoxidation of polyunsaturated lipids , 1986 .

[78]  J. Betts The kinetics of hydrocarbon autoxidation in the liquid phase , 1971 .

[79]  F. Mayo Free radical autoxidations of hydrocarbons , 1968 .

[80]  A. Tobolsky,et al.  The Thermal Decomposition of 2,2'-Azo-bis-isobutyronitrile, , 1958 .

[81]  G. Hammond,et al.  Air Oxidation of Hydrocarbons.1 II. The Stoichiometry and Fate of Inhibitors in Benzene and Chlorobenzene , 1955 .