amination

Summary

Summary: The creation of an amine. It can be produced by the addition of an amino group to an organic compound or reduction of a nitro group.

Top Publications

  1. Shen L, Sun L, Ye S. Highly enantioselective ?-amination of ?,?-unsaturated acyl chlorides with azodicarboxylates: efficient synthesis of chiral ?-amino acid derivatives. J Am Chem Soc. 2011;133:15894-7 pubmed publisher
    The cinchona alkaloid-catalyzed ?-amination of ?,?-unsaturated acyl chlorides with azodicarboxylates to give the corresponding dihydropyridazinones in good yields with high enantioselectivities has been developed...
  2. Li J, Cisar J, Zhou C, Vera B, Williams H, Rodriguez A, et al. Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate. Nat Chem. 2013;5:510-7 pubmed publisher
    ..Here, we describe the use of rhodium(II)-catalysed C-H amination reactions developed by Du Bois to carry out simultaneous structure-activity relationship studies and arming (..
  3. Shrestha R, Mukherjee P, Tan Y, Litman Z, Hartwig J. Sterically controlled, palladium-catalyzed intermolecular amination of arenes. J Am Chem Soc. 2013;135:8480-3 pubmed publisher
    We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects...
  4. Hennessy E, Betley T. Complex N-heterocycle synthesis via iron-catalyzed, direct C-H bond amination. Science. 2013;340:591-5 pubmed publisher
    ..catalyst that leverages the reactivity of iron-borne metal-ligand multiple bonds to promote the direct amination of aliphatic C-H bonds...
  5. Dieckmann A, Richers M, Platonova A, Zhang C, Seidel D, Houk K. Metal-free ?-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates. J Org Chem. 2013;78:4132-44 pubmed publisher
    We have performed a combined computational and experimental study to elucidate the mechanism of a metal-free ?-amination of secondary amines...
  6. Nguyen Q, Nguyen T, Driver T. Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides. J Am Chem Soc. 2013;135:620-3 pubmed publisher
    ..of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction...
  7. Grob J, Nunez J, Dechantsreiter M, Hamann L. One-pot reductive amination and Suzuki-Miyaura cross-coupling of formyl aryl and heteroaryl MIDA boronates in array format. J Org Chem. 2011;76:4930-40 pubmed publisher
    ..heteroaryl MIDA boronates were prepared by a DMSO-free method and used in the first reported one-pot reductive amination-Suzuki-Miyaura cross-coupling sequence...
  8. Tanino T, Ichikawa S, Matsuda A. Synthesis of L-epi-capreomycidine derivatives via C-H amination. Org Lett. 2011;13:4028-31 pubmed publisher
    ..Our synthetic strategy could be a new access to epi-Cpm and its derivatives, which are found in several biologically active natural products. ..
  9. Ng K, Zhou Z, Yu W. Rhodium(III)-catalyzed intermolecular direct amination of aromatic C-H bonds with N-chloroamines. Org Lett. 2012;14:272-5 pubmed publisher
    A Rh(III)-catalyzed direct aromatic C-H amination is achieved using N-chloroamines as a reagent. Furthermore, we also developed a one-pot amination protocol involving in situ chlorination of the secondary amines...

More Information

Publications62

  1. Paradine S, White M. Iron-catalyzed intramolecular allylic C-H amination. J Am Chem Soc. 2012;134:2036-9 pubmed publisher
    A highly selective C-H amination reaction under iron catalysis has been developed...
  2. Raindlová V, Pohl R, Hocek M. Synthesis of aldehyde-linked nucleotides and DNA and their bioconjugations with lysine and peptides through reductive amination. Chemistry. 2012;18:4080-7 pubmed publisher
    ..Bioconjugation of an aldehyde-containing DNA with a lysine-containing tripeptide was achieved through reductive amination in yields of up to 90?% in aqueous phosphate buffer.
  3. Mlynarski S, Karns A, Morken J. Direct stereospecific amination of alkyl and aryl pinacol boronates. J Am Chem Soc. 2012;134:16449-51 pubmed publisher
    The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.
  4. Sun W, Cao P, Mei R, Li Y, Ma Y, Wu B. Palladium-catalyzed unactivated C(sp3)-H bond activation and intramolecular amination of carboxamides: a new approach to ?-lactams. Org Lett. 2014;16:480-3 pubmed publisher
    ..the ?-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated...
  5. Michaudel Q, Thevenet D, Baran P. Intermolecular Ritter-type C-H amination of unactivated sp3 carbons. J Am Chem Soc. 2012;134:2547-50 pubmed publisher
    Intermolecular Ritter-type C-H amination of unactivated sp(3) carbons has been developed. This new reaction proceeds under mild conditions using readily available reagents and an inexpensive source of nitrogen (acetonitrile)...
  6. Barber D, Sanganee H, Dixon D. One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-Mannich/hydroamination cascade. Org Lett. 2012;14:5290-3 pubmed publisher
  7. Liu Y, Yu B, Hao J, Zhou F. Amination of surfaces via self-assembly of dopamine. J Colloid Interface Sci. 2011;362:127-34 pubmed publisher
    ..onto a wide range of inorganic and organic materials, including mica, silica, and Au surface, allowing amination of the surfaces that resemble commercially used aminosilanization...
  8. Matsuda N, Hirano K, Satoh T, Miura M. Copper-catalyzed direct amination of electron-deficient arenes with hydroxylamines. Org Lett. 2011;13:2860-3 pubmed publisher
    The C-H amination of electron-deficient arenes such as polyfluoroarenes and azole compounds with O-acylated hydroxylamines effectively proceeds in the presence of a copper catalyst even at room temperature to provide the corresponding ..
  9. Takahashi K, Yamaguchi D, Ishihara J, Hatakeyama S. Total synthesis of (-)-kaitocephalin based on a Rh-catalyzed C-H amination. Org Lett. 2012;14:1644-7 pubmed publisher
    ..is accomplished in highly stereocontrolled manner via Overman rearrangement, rhodium-catalyzed benzylic C-H amination, pyrrolidine formation involving nucleophilic opening of a cyclic sulfamate, and rhodium-catalyzed allylic C-H ..
  10. Nguyen Q, Sun K, Driver T. Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source. J Am Chem Soc. 2012;134:7262-5 pubmed publisher
    Rhodium(II) dicarboxylate complexes were discovered to catalyze the intramolecular amination of unactivated primary, secondary, or tertiary aliphatic C-H bonds using aryl azides as the N-atom precursor...
  11. Ohyama K, Okawa A, Moriuchi Y, Fujimoto Y. Biosynthesis of steroidal alkaloids in Solanaceae plants: involvement of an aldehyde intermediate during C-26 amination. Phytochemistry. 2013;89:26-31 pubmed publisher
    ..In the present study, the mechanism of C-26 amination was reinvestigated by administering stable isotope labeled compounds, such as (26,26,26,27,27,27-(2)H6)..
  12. Sang P, Xie Y, Zou J, Zhang Y. Copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination: a convenient route to indolo[1,2-c]quinazoline derivatives. Org Lett. 2012;14:3894-7 pubmed publisher
    ..derivatives has been developed by copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination. The protocol uses readily available 2-(2-halophenyl)-1H-indoles and (aryl)methanamines as the starting ..
  13. Lu H, Hu Y, Jiang H, Wojtas L, Zhang X. Stereoselective radical amination of electron-deficient C(sp3)-H bonds by Co(II)-based metalloradical catalysis: direct synthesis of ?-amino acid derivatives via ?-C-H amination. Org Lett. 2012;14:5158-61 pubmed publisher
    The cobalt(II) complex of 3,5-Di(t)Bu-IbuPhyrin, [Co(P1)], is an effective catalyst for intramolecular amination of electron-deficient C-H bonds, including those adjacent to electron-withdrawing CO(2)R, C(O)NR(2), C(O)R, and CN groups, ..
  14. Zhang Y, Kuang M, Zhang L, Yang P, Lu H. An accessible protocol for solid-phase extraction of N-linked glycopeptides through reductive amination by amine-functionalized magnetic nanoparticles. Anal Chem. 2013;85:5535-41 pubmed publisher
    ..Herein, we reported a novel protocol of solid-phase extraction of glycopeptides through a reductive amination reaction by employing the easily accessible 3-aminopropyltriethoxysilane (APTES)-functionalized magnetic ..
  15. Qi H, Chen D, Ye J, Huang J. Electrochemical technique and copper-promoted transformations: selective hydroxylation and amination of arylboronic acids. J Org Chem. 2013;78:7482-7 pubmed publisher
    ..We propose that anodic oxidation could have played an important role in these transformations. ..
  16. Cecere G, König C, Alleva J, MacMillan D. Enantioselective direct ?-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling. J Am Chem Soc. 2013;135:11521-4 pubmed publisher
    The direct, asymmetric ?-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis...
  17. Nguyen M, Smith A. Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents. Org Lett. 2013;15:4872-5 pubmed publisher
    The development and validation of copper-catalyzed, electrophilic amination of aryl and heteroaryl organolithiums with N,N-dialkyl-O-benzoylhydroxylamines have been achieved exploiting recoverable siloxane transfer agents...
  18. Fier P, Hartwig J. Selective C-H fluorination of pyridines and diazines inspired by a classic amination reaction. Science. 2013;342:956-60 pubmed publisher
    ..Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.
  19. Shang M, Zeng S, Sun S, Dai H, Yu J. Ru(II)-catalyzed ortho-C-H amination of arenes and heteroarenes at room temperature. Org Lett. 2013;15:5286-9 pubmed publisher
    The Ru(II)-catalyzed ortho-C-H amination directed by a weakly coordinating amide auxiliary with O-benzoyl hydroxylamines at room temperature has been achieved...
  20. Rigoli J, Weatherly C, Alderson J, Vo B, Schomaker J. Tunable, chemoselective amination via silver catalysis. J Am Chem Soc. 2013;135:17238-41 pubmed publisher
  21. Enomoto T, Girard A, Yasui Y, Takemoto Y. Gold(I)-catalyzed tandem reactions initiated by hydroamination of alkynyl carbamates: application to the synthesis of nitidine. J Org Chem. 2009;74:9158-64 pubmed publisher
  22. Hooper M, Utsunomiya M, Hartwig J. Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides. J Org Chem. 2003;68:2861-73 pubmed
    Detailed studies have been conducted to determine the activity of palladium catalysts for the amination of five-membered heterocyclic halides and to determine the factors that control the scope of this reaction...
  23. Dalpathado D, Jiang H, Kater M, Desaire H. Reductive amination of carbohydrates using NaBH(OAc)3. Anal Bioanal Chem. 2005;381:1130-7 pubmed
    An improved protocol for reductive amination of carbohydrates is developed. This derivatization facilitates the detection of oligosaccharides in HPLC-UV and mass spectrometric applications by enhancing the signal of the carbohydrates...
  24. Hultzsch K. Catalytic asymmetric hydroamination of non-activated olefins. Org Biomol Chem. 2005;3:1819-24 pubmed
    ..This review highlights recent progress in the development of early transition metal catalysts for the asymmetric hydroamination of non-activated alkenes. ..
  25. Charles M, Schultz P, Buchwald S. Efficient pd-catalyzed amination of heteroaryl halides. Org Lett. 2005;7:3965-8 pubmed
    The Pd-catalyzed amination of a variety of heteroaryl halides has been accomplished by utilizing bulky electron-rich biaryl phosphine ligands...
  26. Hennessy E, Buchwald S. Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's disease via palladium-catalyzed amination. J Org Chem. 2005;70:7371-5 pubmed
    ..We have developed a synthetic route to DAPH and structurally related analogues that employs palladium-catalyzed amination as the key bond-forming step...
  27. Fraunhoffer K, White M. syn-1,2-Amino alcohols via diastereoselective allylic C-H amination. J Am Chem Soc. 2007;129:7274-6 pubmed
  28. Broberg A. High-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry for analysis of oligosaccharides derivatized by reductive amination and N,N-dimethylation. Carbohydr Res. 2007;342:1462-9 pubmed
    Milk oligosaccharides derivatized by reductive amination with benzylamine followed by N,N-dimethylation (DMBA-oligosaccharides), were analyzed by high-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry (..
  29. Zhang C, De C, Mal R, Seidel D. Alpha-amination of nitrogen heterocycles: ring-fused aminals. J Am Chem Soc. 2008;130:416-7 pubmed
  30. Organ M, Abdel Hadi M, Avola S, Dubovyk I, Hadei N, Kantchev E, et al. Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI. Chemistry. 2008;14:2443-52 pubmed publisher
    Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination protocols mediated by Pd-PEPPSI precatalysts is described...
  31. Benfatti F, Cardillo G, Gentilucci L, Mosconi E, Tolomelli A. Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates. Org Lett. 2008;10:2425-8 pubmed publisher
    The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism...
  32. Zalatan D, Du Bois J. A chiral rhodium carboxamidate catalyst for enantioselective C-H amination. J Am Chem Soc. 2008;130:9220-1 pubmed publisher
    ..complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters...
  33. Olson D, Du Bois J. Catalytic C-H amination for the preparation of substituted 1,2-diamines. J Am Chem Soc. 2008;130:11248-9 pubmed publisher
    ..This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction...
  34. Jordan Hore J, Johansson C, Beck E, Gaunt M. Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature. J Am Chem Soc. 2008;130:16184-6 pubmed publisher
    We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems...
  35. Wu B, Szymanski W, Wietzes P, De Wildeman S, Poelarends G, Feringa B, et al. Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivatives. Chembiochem. 2009;10:338-44 pubmed publisher
    ..The internal 5-methylene-3,5-dihydroimidazol-4-one (MIO) cofactor is essential for the PAM-catalysed amination reactions. The regioselectivity of amination reactions was influenced by the nature of the ring substituent.
  36. Powell D, Fan H. Copper-catalyzed amination of primary benzylic C-H bonds with primary and secondary sulfonamides. J Org Chem. 2010;75:2726-9 pubmed publisher
    A room-temperature, copper-catalyzed amination of primary benzylic C-H bonds with primary and secondary sulfonamides is described...
  37. Zalatan D, Du Bois J. Understanding the differential performance of Rh2(esp)2 as a catalyst for C-H amination. J Am Chem Soc. 2009;131:7558-9 pubmed publisher
    Catalytic amination of saturated C-H bonds is performed efficiently with the use of Rh(2)(esp)(2)...
  38. Lu H, Tao J, Jones J, Wojtas L, Zhang X. Cobalt(II)-catalyzed intramolecular C-H amination with phosphoryl azides: formation of 6- and 7-membered cyclophosphoramidates. Org Lett. 2010;12:1248-51 pubmed publisher
    A highly effective Co(II)-based system has been developed for catalytic intramolecular C-H amination with phosphoryl azides without the need of terminal oxidant or other additives, resulting in the high-yielding production of ..
  39. Jiao J, Zhang X, Chang N, Wang J, Wei J, Shi X, et al. A facile and practical copper powder-catalyzed, organic solvent- and ligand-free Ullmann amination of aryl halides. J Org Chem. 2011;76:1180-3 pubmed publisher
    A facile and practical method that the copper powder-catalyzed Ullmann amination of aryl halides with aqueous methylamine under organic solvent- and ligand-free condition at 100 °C and in air gave N-arylamines as sole products in good ..
  40. Bonnamour J, Bolm C. Iron(II) triflate as a catalyst for the synthesis of indoles by intramolecular C-H amination. Org Lett. 2011;13:2012-4 pubmed publisher
    A practical iron-catalyzed intramolecular C-H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.
  41. Suhadolnik R, Pornbanlualap S, Baker D, Tiwari K, Hebbler A. Stereospecific 2'-amination and 2'-chlorination of adenosine by Actinomadura in the biosynthesis of 2'-amino-2'-deoxyadenosine and 2'-chloro-2'-deoxycoformycin. Arch Biochem Biophys. 1989;270:374-82 pubmed
    ..Mechanisms for the regioselective modification of the C-2' hydroxyl group and stereospecific insertion of the amino and chloro groups are discussed. ..
  42. Henderson J, Buchwald S. Efficient Pd-catalyzed amination reactions for heterocycle functionalization. Org Lett. 2010;12:4442-5 pubmed publisher
    The Pd-catalyzed amination of unprotected benzo-fused heterocycles is reported, which allows for greater flexibility and efficiency in the modification of this important class of molecules...
  43. Henderson J, McDermott S, Buchwald S. Palladium-catalyzed amination of unprotected halo-7-azaindoles. Org Lett. 2010;12:4438-41 pubmed publisher
    ..Using palladium precatalysts recently reported by our group, such reactions are easily accomplished under mild conditions that can be applied to cross-coupling reactions with a wide array of aliphatic and aromatic amines. ..
  44. Kawano T, Hirano K, Satoh T, Miura M. A new entry of amination reagents for heteroaromatic C-H bonds: copper-catalyzed direct amination of azoles with chloroamines at room temperature. J Am Chem Soc. 2010;132:6900-1 pubmed publisher
    Chloroamine serves as an efficient amination reagent to the heteroaromatic C-H bond of azole under copper catalysis even at room temperature...
  45. Tan Y, Hartwig J. Palladium-catalyzed amination of aromatic C-H bonds with oxime esters. J Am Chem Soc. 2010;132:3676-7 pubmed publisher
    We report a conceptually new approach to the direct amination of aromatic C-H bonds. In this process, an oxime ester function reacts with an aromatic C-H bond under redox-neutral conditions to form, in the case studied, an indole product...
  46. Pahadi N, Paley M, Jana R, Waetzig S, Tunge J. Formation of N-alkylpyrroles via intermolecular redox amination. J Am Chem Soc. 2009;131:16626-7 pubmed publisher
    A wide variety of aldehydes, ketones, and lactols undergo redox amination when allowed to react with 3-pyrroline in the presence of a mild Brønsted acid catalyst...
  47. Mei T, Wang X, Yu J. Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants. J Am Chem Soc. 2009;131:10806-7 pubmed publisher
    Pd(II)-catalyzed intramolecular amination of arenes is developed using either a one- or two-electron oxidant. The reaction protocol tolerates a wide range of deactivating groups including acetyl, cyano, and nitro groups...
  48. Angelov T, Guainazzi A, SCHARER O. Generation of DNA interstrand cross-links by post-synthetic reductive amination. Org Lett. 2009;11:661-4 pubmed publisher
    ..bearing acetaldehyde groups were incorporated into complementary strands of DNA and cross-link formation induced by double reductive amination. Our strategy enables the synthesis of major groove cross-links in high yields and purity.
  49. Shen Q, Hartwig J. [(CyPF-(t)Bu)PdCl2]: an air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides. Org Lett. 2008;10:4109-12 pubmed publisher
    ..Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups. ..
  50. Reed S, White M. Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis. J Am Chem Soc. 2008;130:3316-8 pubmed publisher
  51. Inamoto K, Saito T, Katsuno M, Sakamoto T, Hiroya K. Palladium-catalyzed C-H activation/intramolecular amination reaction: a new route to 3-aryl/alkylindazoles. Org Lett. 2007;9:2931-4 pubmed
    A method for the catalytic C-H activation of hydrazone compounds followed by intramolecular amination is described...
  52. Zou B, Yuan Q, Ma D. Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process. Angew Chem Int Ed Engl. 2007;46:2598-601 pubmed
  53. Grasa G, Viciu M, Huang J, Nolan S. Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems. J Org Chem. 2001;66:7729-37 pubmed
    Nucleophilic N-heterocyclic carbenes have been conveniently used as catalyst modifiers in amination reactions involving aryl chlorides, aryl bromides, and aryl iodides with various nitrogen-containing substrates...