- Mercuration demercuration of aliphatic isocyanates: A new mild route to primary amines
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Aliphatic isocyanates react with mercury acetate in THF/H2O and successively with sodium boro hydride to give aliphatic primary amines in good yields in short reaction times with high stereo control.
- Malanga, Corrado,Urso, Andrea,Lardicci, Luciano
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Read Online
- A convenient Hofmann reaction of carboxamides and cyclic imides mediated by trihaloisocyanuric acids
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A simple, efficient and pot-economic approach in a single vessel has been developed for conversion of aromatic and aliphatic carboxamides into primary amines with one fewer carbom atom (Hofmann reaction) in 38–89 % yield by reacting with trichloro- or tribromoisocyanuric acid and sodium hydroxide in aqueous acetonitrile. Under the same reaction conditions, cyclic imides gave amino acids (69–83 %). The role of the trihaloisocyanuric acids is the in situ generation of N-haloamides, key-intermediates for the Hofmann reaction. The scalability of the methodology was demonstrated by a multigram-scale transformation of phthalimide into anthranilic acid in 77 % yield.
- Bastos, Gustavo A.,de Mattos, Marcio C.S.
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- Facile synthesis of controllable graphene-co-shelled reusable Ni/NiO nanoparticles and their application in the synthesis of amines under mild conditions
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The primary objective of many researchers in chemical synthesis is the development of recyclable and easily accessible catalysts. These catalysts should preferably be made from Earth-abundant metals and have the ability to be utilised in the synthesis of pharmaceutically important compounds. Amines are classified as privileged compounds, and are used extensively in the fine and bulk chemical industries, as well as in pharmaceutical and materials research. In many laboratories and in industry, transition metal catalysed reductive amination of carbonyl compounds is performed using predominantly ammonia and H2. However, these reactions usually require precious metal-based catalysts or RANEY nickel, and require harsh reaction conditions and yield low selectivity for the desired products. Herein, we describe a simple and environmentally friendly method for the preparation of thin graphene spheres that encapsulate uniform Ni/NiO nanoalloy catalysts (Ni/NiO?C) using nickel citrate as the precursor. The resulting catalysts are stable and reusable and were successfully used for the synthesis of primary, secondary, tertiary, and N-methylamines (more than 62 examples). The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, and H2 under very mild industrially viable and scalable conditions (80 °C and 1 MPa H2 pressure, 4 h), offering cost-effective access to numerous functionalized, structurally diverse linear and branched benzylic, heterocyclic, and aliphatic amines including drugs and steroid derivatives. We have also demonstrated the scale-up of the heterogeneous amination protocol to gram-scale synthesis. Furthermore, the catalyst can be immobilized on a magnetic stirring bar and be conveniently recycled up to five times without any significant loss of catalytic activity and selectivity for the product.
- Cui, Zhibing,Liu, Jianguo,Liu, Qiying,Ma, Longlong,Singh, Thishana,Wang, Chenguang,Wang, Nan,Zhu, Yuting
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supporting information
p. 7387 - 7397
(2020/11/19)
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- Method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds
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The invention discloses a method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds. The method comprises the following steps: 1) mixing nickel nitrate hexahydrate, citric acid and an organic solvent, carrying out heating and stirring until a colloidal material is obtained, drying the colloidal material, roasting the colloidal material in a protective atmosphere, pickling, washing and drying a roasted product, and performing a partial oxidation reaction on a dried product in an oxygen-nitrogen mixed atmosphere to obtain a catalyst for a reductive amination reaction; and 2) mixing aldehyde or ketone compounds, a methanol solution of ammonia and the reductive amination reaction catalyst, introducing hydrogen, and carrying out a reductive amination reaction. The method has the advantages of high primary amine yield, high selectivity, wide aldehyde ketone substrate range, short reaction time, mild reaction conditions, low cost, greenness, economicalperformance and the like; the used reductive amination reaction catalyst can be recycled more than 10 times, and the catalytic activity of the catalyst is not obviously changed in gram-level reactions; and the method is suitable for large-scale application.
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Paragraph 0027-0030; 0051-0055
(2020/05/30)
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- Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
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While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
- Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
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supporting information
p. 8059 - 8064
(2020/11/02)
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- A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation
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Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.
- Formenti, Dario,Mocci, Rita,Atia, Hanan,Dastgir, Sarim,Anwar, Muhammad,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
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supporting information
p. 15589 - 15595
(2020/10/02)
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- Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
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The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.
- Hyodo, Kengo,Hasegawa, Genna,Maki, Hiroya,Uchida, Kingo
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supporting information
p. 2818 - 2822
(2019/04/25)
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- PRODUCTION METHOD OF PRIMARY AMINE COMPOUND
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PROBLEM TO BE SOLVED: To provide a simple production method of a primary amine compound unnecessary for complicated procedures and toxic sodium azide or the like. SOLUTION: A production method of a primary amine compound includes a step for reacting a ketone compound and an oxime compound in the presence of alcohol and an acid catalyst. Preferably, the acid catalyst is hydrochloric acid, sulfuric acid, methanesulfonic acid, camphorsulfonic acid, a tosyl acid hydrate, trifluoromethane sulfonic acid or a boron trifluoride diethyl ether complex. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0029
(2019/09/20)
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- Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis
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Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.
- Palo-Nieto, Carlos,Afewerki, Samson,Anderson, Mattias,Tai, Cheuk-Wai,Berglund, Per,Córdova, Armando
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p. 3932 - 3940
(2016/07/06)
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- A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands
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A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.
- Adam, Rosa,Bheeter, Charles Beromeo,Jackstell, Ralf,Beller, Matthias
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p. 1329 - 1334
(2016/04/20)
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- Amination of ω-Functionalized Aliphatic Primary Alcohols by a Biocatalytic Oxidation-Transamination Cascade
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Amination of non-activated aliphatic fatty alcohols to the corresponding primary amines was achieved through a five-enzyme cascade reaction by coupling a long-chain alcohol oxidase from Aspergillus fumigatus (LCAO-Af) with a ω-transaminase from Chromobacterium violaceum (ω-TA-Cv). The alcohol was oxidized at the expense of molecular oxygen to yield the corresponding aldehyde, which was subsequently aminated by the PLP-dependent ω-TA to yield the final primary amine product. The overall cascade was optimized with respect to pH, O2 pressure, substrate concentration, decomposition of H2O2 (derived from alcohol oxidation), NADH regeneration, and biocatalyst ratio. The substrate scope of this concept was investigated under optimized conditions by using terminally functionalized C4-C11 fatty primary alcohols bearing halogen, alkyne, amino, hydroxy, thiol, and nitrile groups.
- Pickl, Mathias,Fuchs, Michael,Glueck, Silvia M.,Faber, Kurt
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p. 3121 - 3124
(2015/10/19)
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- Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids
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A new (S)-enantioselective ω-transaminase (ω-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged ω-TA (HBV-ω-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-α-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-ω-TA as the catalyst and isopropylamine or (S)-α-MBA as amino donor. Notably, HBV-ω-TA catalyzed the amino transfer to β-keto esters to give optically pure β-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained.
- Jiang, Jinju,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming
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- PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRILE FUNCTIONS
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The production of compounds comprising nitrile functions and of cyclic imide compounds is described. Further described, is the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, optionally of natural and renewable origin, and from a mixture N of dinitriles comprising 2-methylglutaronitrile (MGN), 2-ethylsuccinonitrile (ESN) and adiponitrile (AdN).
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Paragraph 0067
(2013/08/15)
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- SYNTHESIS OF OMEGA-AMINO CARBOXYLIC ACIDS AND THEIR ESTERS FROM UNSATURATED FATTY ACID DERIVATIVES
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The invention relates to a process for preparing omega-amino acids or their esters, which is characterized by the following steps: c) ozonolysis of unsaturated fatty acids or fatty acid derivatives,d) reductive amination of the reaction mixture obtained from the reaction with ozone, to give the omega-amino acid or ester thereof, the reaction being carried out with a C1-C5 alcohol in a mixture with at least 0.5% by weight of water as solvent, based on the total amount of solvent.
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Paragraph 0034; 0035
(2013/07/05)
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- Two iron catalysts are better than one: A general and convenient reduction of aromatic and aliphatic primary amides
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It takes two: For the reduction of amides to amines iron catalysts were developed. A combination of two different iron catalysts made possible the challenging reduction of primary amides (see picture). Copyright
- Das, Shoubhik,Wendt, Bianca,Moeller, Konstanze,Junge, Kathrin,Beller, Matthias
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supporting information; experimental part
p. 1662 - 1666
(2012/05/05)
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- PRODUCTION OF AMINES
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A process for the hydrogenation of carboxylic acids and/or derivatives, particularly amides, is described. The process includes reacting an acid or derivative such as an amide with a source of hydrogen in the presence of a catalyst system. The catalyst system obtainable by combining: (a) a source of ruthenium, and (b) a phosphine compound of general Formula I: (Formula I). The hydrogenation reaction is carried out in the presence of a low concentration of water or at low pressure or in the presence of a source of ammonia or the hydrogenation reaction is carried out in the absence of water or a combination of these factors is utilised. The invention also relates to the use of ammonia in the production of primary amines by hydrogenation of carboxylic acids and/or derivatives thereof or a process for the production of primary amines generally.
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Page/Page column 26
(2008/06/13)
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- Salt suitable for an acid generator and a chemically amplified positive resist composition containing the same
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The present invention provides a salt represented by the formula (I): wherein P1, P2 and P3 each independently represent a C1-C30 alkyl group which may be substituted with at least one selected from a hydroxyl group, a C3-C12 cyclic hydrocarbon group and a C1-C12 alkoxy group, or a C3-C30 cyclic hydrocarbon group which may be substituted with at least one selected from a hydroxyl group and a C1-C12 alkoxy group, provided that all of P1, P2 and P3 are not simultaneously phenyl groups which may be substituted, Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, and R represents a group represented by the formula: wherein A1 represents —OH or —Y1—OH, n represents an integer of 1 to 9, and Y1 represents a divalent C1-C6 saturated aliphatic hydrocarbon group; a group represented by the formula: wherein ring X1 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —CO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X2 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which a hydrogen atom of one —CH2— group is substituted with a hydroxyl group, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X3 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —COO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group, and m represents an integer of 0 to 12; or a group represented by the formula: wherein ring X4 represents a C6-C30 polycyclic hydrocarbon group having tricycle or more, and at least one hydrogen atom in the polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group or a cyano group, and l represents an integer of 1 to 12. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
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- The synthesis of amines by the homogeneous hydrogenation of secondary and primary amides
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Amides can be hydrogenated to amines using a catalyst prepared in situ from [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane; water is required to stabilize the catalyst and primary amines can only be formed (selectivity up to 85%) if ammonia is also present. The Royal Society of Chemistry.
- Nú?ez Magro, Angel A.,Eastham, Graham R.,Cole-Hamilton, David J.
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p. 3154 - 3156
(2008/02/13)
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- Non-metallocene compounds, method for the production thereof and use of the same for the polymerisation of olefins
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The invention relates to a method for producing special transition metal compounds, to novel transition metal compounds and to the use of the same for the polymerisation of olefins.
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- Indium Mediated Reduction of Nitro and Azide Groups in the Presence of HCl in Aqueous Media
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Indium mediated reduction of azide and nitro groups in the presence of HCl (1.5 equiv based on indium) at room temperature in aqueous THF successfully provided the corresponding amine in high to quantitative yields. Under the some reaction conditions, selective reduction of azide and nitro group in the presence of vinyl group could be accomplished.
- Lee, Jung Gyu,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Kang, Yonghan,Cho, Yong Seo
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- Reductions with lithium in low molecular weight amines and ethylenediamine
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Reductions of several types of compounds with lithium and ethylenediamine using low molecular weight amines as solvent are described. In all cases 1 mol of ethylenediamine or N,N'-dimethylethylenediamine per gram-atom of lithium was used. In some cases it was beneficial to add an alcohol as a proton donor. These reaction conditions were applied to the debenzylation of N-benzylamide and lactams which are refractory to hydrogenolysis with hydrogen and a catalyst. N-Benzylpilolactam 2, synthesized from pilocarpine hydrochloride in refluxing benzylamine, was debenzylated in good yield using 10 gram-atoms of lithium per mole (10 Li/mol) of 2 in n-propylamine. The debenzylation of N-benzyl-N-methyldecanoic acid amide, 4 (6 Li/mol), in t-butylamine/N,N'-dimethylethylenediamine gave N-methyldecanoic acid amide 6 in 70% yield. Alternatively, reduction of 4 (7 Li/mol) in t-butanol/n-propylamine/ethylenediamine gave n-decanal 12 in 36% yield. Using the same conditions, thioanisole, 1-adamantane-p-toluenesulfonamide, and 1-adamantane methyl p-toluenesulfonate were reduced with 3, 7, and 7.2 Li/mol of compound to give thiophenol (74%), adamantamine (91%), and 1-adamantane methanol (75%), respectively. In this solvent system naphthalene and 3-methyl-2-cyclohexene-1-one were reduced to isotetralin (74%) and 3-methyl cyclohexanone (quantitative) with 5 and 2.2 Li/mol of starting compound, respectively. Oximes and O-methyloximes were reduced to their corresponding amines using 5 and 8 Li/mol of compound, respectively. Anisole was also reduced to 1-methoxy-1,4-cyclohexadiene with 2.5 Li/mol of anisole. Undecanenitrile was reduced to undecylamine with 8.6 Li/mol. Additionally, a base-catalyzed formation of imidazolines from a nitrile and ethylenediamine was also explored.
- Garst,Dolby,Esfandiari,Fedoruk,Chamberlain,Avey
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p. 7098 - 7104
(2007/10/03)
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- Lithium and amine dissolving metal reduction
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The invention is directed to a process for reducing or reductively cleaving an organic compound susceptible to dissolving metal reduction comprising exposing the organic compound to a solution of lithium in a polyamine including at least two amino groups, selected from the group consisting of primary and secondary amino groups and mixtures thereof, e.g. ethylenediamine and R--NH2, optionally containing a lower alkyl alcohol, wherein R is chosen from the group consisting of ethyl, propyl, and butyl, including all straight and branched chain isomers thereof, for a time sufficient to effect reduction.
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- Convenient methods for the reduction of amides, nitriles, carboxylic esters, acids and hydroboration of alkenes using NaBH4/I2system
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Reaction of amides with NaBH4-I2 system in THF gives the corresponding amines in 70-76% yields. Reduction of nitriles yields the corresponding amines in 70-75% yields. The I2/NaBH4 system is useful in the hydrocarboration of olefins and the corresponding alcohols are obtained in 78-92% yields after H2O2/OH- oxidation. The reagent system is also useful for the reduction of carboxylic esters and acids to the corresponding alcohols in 60-90% yields.
- Bhanu Prasad,Bhaskar Kanth,Periasamy, Mariappan
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p. 4623 - 4628
(2007/10/02)
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- Novel Borane-Selenium Complex: Highly Selective Reduction of Tertiary Amides and Nitriles to the Corresponding Amines with Sodium Borohydride-Dialkylselenium Dibromide
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The reaction of sodium borohydride with bis(2-bromoethyl)selenium dibromide and/or diethylselenium dibromide in tetrahydrofuran (THF) gave borane.Treatment of tertiary amides with mixtures of sodium borohydride and either of the dibromides in THF gave the corresponding amines.Similar reactions with secondary and primary amides did not proceed.Furthermore, under similar reduction conditions, the reaction of nitriles with the above reagents also gave the corresponding primary amines.
- Akabori, Sadatoshi,Takanohashi, Yoshinori
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p. 479 - 482
(2007/10/02)
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- REACTION OF AROMATIC DI- AND TETRACARBOXYLIC ANHYDRIDES WITH AMIDES
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In the reaction of aromatic di- and tetracarboxylic anhydrides containing carboxyl groups at the ortho and peri position with amides the corresponding mono- and diimides were obtained.The reaction of phthalic anhydride with formamide, leading to phthalimide, takes place with the intermediate formation of N-formylphthalamic acid.
- Ganin, E. V.,Makarov, V. F.,Nikitin, V. I.
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p. 981 - 983
(2007/10/02)
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- SODIUM BROMITE: A NEW REAGENT FOR THE HOFMANN DEGRADATION OF AMIDES
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Amines are prepared in fairly good yields by the reaction of amides with sodium bromide in the presence of catalytic amount of sodium bromite in aqueous sodium hydroxide.The scope and limitations are also presented.
- Kajigaeshi, Shoji,Nakagawa, Takashi,Fijusaki, Shizuo,Nishida, Akiko,Noguchi, Michihiko
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p. 713 - 714
(2007/10/02)
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- Preparation of 3,3,3-trifluoropropene-1
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Process for preparing 3,3,3-trifluoropropene-1 by contacting and reacting at least one of 1,1,1,3-tetrachloropropane, 1,1,3-trichloropropene-1 and 3,3,3-trichloropropene-1 and HF, under autogenous pressure, at 140°-250° C., in the presence of at least a catalytic amount of an organic monoamine, a salt of the monoamine or an alkylene diamine, said monoamine and salt being of the formula R3 N.(R'X)n wherein n is 0 or 1, X is an appropriate anion, each R and R' is selected independently from H, alkyl of 1-16 carbon atoms, cycloalkyl of 6-10 carbon atoms, aryl of 6-10 carbon atoms and alkylaryl of 6-10 carbon atoms, provided, however, when n is 0, no more than two of the R groups are H and when n is 1, no more than three of the R and R' groups are H, and provided, however, R3 N taken jointly is piperidine, pyrrolidine, indoline, isoindoline, pyridine, quinoline or isoquinoline, each optionally substituted with 1-3 methyl groups, said alkylene diamine being of the formula R"2 N--CH2 --NR"2 wherein m is 2-10 and each R" is selected independently from H, alkyl of 1-4 carbon atoms and phenyl, provided, however, when m is 2, each R" is selected independently from alkyl of 1-4 carbon atoms and phenyl.
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