- Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions
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Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.
- Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Rumi, Saeki,Sato, Katsutoshi,Shiraishi, Masaya
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supporting information
p. 81 - 84
(2022/01/12)
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- Direct Reductive N-Functionalization of Aliphatic Nitro Compounds
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The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic amination of zinc organyls.
- Rauser, Marian,Ascheberg, Christoph,Niggemann, Meike
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p. 3970 - 3974
(2018/02/26)
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- Facile Synthesis and Isolation of Secondary Amines via a Sequential Titanium(IV)-Catalyzed Hydroamination and Palladium-Catalyzed Hydrogenation
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An atom economical and catalytic route for the synthesis of aryl- and alkyl-substituted secondary amines has been developed. Using a bis(amidate)bis(amido)titanium(IV) precatalyst, the hydroamination of terminal alkynes with a range of amines results in the selective formation of the anti-Markovnikov product. The crude enamine/imine mixtures are effectively hydrogenated using palladium on carbon (Pd/C) and H2 to afford the corresponding secondary amine in excellent yields. Simple work-up procedures allow for the isolation of pure compounds while avoiding purification via column chromatography.
- Lui, Erica K. J.,Schafer, Laurel L.
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supporting information
p. 713 - 718
(2016/03/09)
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- Solid base catalyzed highly efficient N-alkylation of amines with alcohols in a solvent-free system
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Different from any other catalytic systems containing transition metals and additives, sodium hydroxide itself was found to be a unique and effective catalyst for the solvent-free synthesis of the secondary amines via the N-alkylation of amines with alcohols. For the reaction of aniline with benzyl alcohol, 99.6 mol% conversion of aniline and 99.5% selectivity of the product were achieved under optimal conditions. Also, high conversion and selectivity could be acquired for the N-alkylations of various amines with alcohols, implying the universality of this methodology. Mechanistic studies revealed that this novel reaction most possibly proceeds with a base-catalyzed mechanism.
- Lu,Sun,Wei,Peng,Zhou,Xia
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- Selective N-alkylation of primary amines with R-NH2·HBr and alkyl bromides using a competitive deprotonation/protonation strategy
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Monoalkylation of primary amines using amine hydrobromides and alkyl bromides has been carried out. Under controlled reaction conditions the reactant primary amine was selectively deprotonated and made available for reaction, while the newly generated secondary amine remained protonated, and did not participate in alkylation further. Reaction was carried out under mild reaction conditions and was applicable to a wide range of primary amines and alkyl bromides.
- Bhattacharyya, Shubhankar,Pathak, Uma,Mathur, Sweta,Vishnoi, Subodh,Jain, Rajeev
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p. 18229 - 18233
(2014/05/20)
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- Structure-activity relationships of small molecule inhibitors of RAGE-Aβ binding
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The Receptor for Advanced Glycation Endproducts ('RAGE') mediates transport of amyloid-β peptide (Aβ) into the brain, and is therefore an important target for the development of therapeutic agents for Alzheimer's disease. We describe structure-activity relationships for inhibition of RAGE-Aβ binding, derived from the analysis of a library of tertiary amides.
- Ross, Nathan T.,Deane, Rashid,Perry, Sheldon,Miller, Benjamin L.
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p. 7653 - 7658
(2013/08/23)
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- Catalytic C - H amination with unactivated amines through copper(II) amides
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En route to catalysis: Two equivalents of the three-coordinate copper(II) amide [(Cl2NN)Cu]-NHAd participate in stoichiometric C - H amination by a H-atom abstraction/radical capture sequence. This active species may be generated through a copper(II) tert-butoxide intermediate to allow for the unprecedented catalytic amination of sp3-C - H bonds with unactivated alkylamines. This method greatly expands the range of amines for catalytic C - H amination since most protocols require N-based electron-withdrawing groups.
- Wiese, Stefan,Badiei, Yosra M.,Gephart, Raymond T.,Mossin, Susanne,Varonka, Matthew S.,Melzer, Marie M.,Meyer, Karsten,Cundari, Thomas R.,Warren, Timothy H.
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supporting information; experimental part
p. 8850 - 8855
(2011/02/24)
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- Efficient and clean gold-catalyzed one-pot selective n-alkylation of amines with alcohols
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Atom-efficient direct N-alkylation: An environmentally clean one-pot selective N-alkylation of amines with an equimolar amount of alcohols via a hydrogen autotransfer pathway was achieved over a titania-supported gold catalyst system in good to excellent yields without additive (see scheme).
- He, Lin,Lou, Xia-Bing,Ni, Ji,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian
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supporting information; experimental part
p. 13965 - 13969
(2011/02/23)
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- Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines
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A versatile and highly atom economical catalytic system consisting of [Cp*IrCl2]2/NaHCO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp*IrCl2]2 (1.0 mol % Ir) and NaHCO3 (1.0 mol %) in toluene at 110 °C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described.
- Fujita, Ken-ichi,Enoki, Youichiro,Yamaguchi, Ryohei
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p. 1943 - 1954
(2008/09/17)
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- UREA GLUCOKINASE ACTIVATORS
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The invention provides a compound of general formula (I) wherein the substituents are defined futher in the application, as well as further embodiments hereof described in the attached embodiments. The present invention also provides use of the compounds
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Page/Page column 78-79
(2008/06/13)
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- N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex
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A new effective catalytic system consisting of [Cp*IrCl2]2/K2CO3 (Cp=pentamethylcyclopentadienyl) for the N-alkylation of primary amines with alcohols has been developed. As an example, the reaction of aniline with benzyl alcohol in the presence of [Cp*IrCl2]2 (5.0 mol%Ir) and K2CO3 (5.0 mol%) in toluene at 110°C for 17 h gave benzylaniline in an isolated yield of 88%.
- Fujita, Ken-Ichi,Li, Zhenzi,Ozeki, Naohiro,Yamaguchi, Ryohei
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p. 2687 - 2690
(2007/10/03)
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- Preparation of secondary amines by reductive animation with metallic magnesium
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A novel and efficient method for the preparation of secondary amines by reductive animation of carbonyl compounds with primary amines has been developed. The reduction, effected with metallic magnesium in methanol, utilizing triethylamine-acetic acid as a buffer, gave pure secondary amines, mostly in good yields (65-80%). No formation of tertiary amines or alcohols was observed. Use of ammonium acetate as an amino component gave primary amines in modest yields (ca. 50%), together with variable amounts of secondary amines. Enamines failed to undergo reduction. The method is inexpensive, relatively rapid, operationally simple and suitable for large-scale preparations. In addition, a simple method for separation of primary amines from secondary ones has been developed.
- Micovic, Ivan V.,Ivanovic,Roglic, Goran M.,Kiricojevic, Vesna D.,Popovic, Jelena B.
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p. 265 - 269
(2007/10/03)
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- Radical cyclisations of imines and hydrazones
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Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.
- Bowman, W. Russell,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
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p. 7959 - 7980
(2007/10/02)
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- N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
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The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 deg C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents , (EtO)2CO, CH2=CHCO2Me, , PhCH=NPh, MeI, and CH2=CHCH2Br> to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5.When the reductive opening and the reaction with electrophiles were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with the same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
- Almena, Juan,Foubelo, Francisco,Yus, Miguel
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p. 3210 - 3215
(2007/10/02)
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- Mono-N-alkylation of α-Aminoacetonitriles. A Novel Route to Unsymmetrical Secondary Amines
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Mannich-type condensation products of an aldehyde with an α-aminoacetonitrile and benzotriazole are treated with sodium borohydride or with a Grignard reagent to give unsymmetrical N,N-dialkylaminoacetonitriles, which, on decyanomethylation provide unsymmetrical secondary amines.
- Katritzky, Alan R.,Latif, Muhammad,Urogdi, Laszlo
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p. 667 - 672
(2007/10/02)
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