- Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation
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There is a strong incentive for environmentally benign and sustainable production of organic nitriles to avoid the use of toxic cyanides. Here we report that manganese oxide nanorod-supported single-site Ru catalysts are active, selective, and stable for oxidative cyanation of various alcohols to give the corresponding nitriles with molecular oxygen and ammonia as the reactants. The very low amount of Ru (0.1 wt %) with atomic dispersion boosts the catalytic performance of manganese oxides. Experimental and theoretical results show how the Ru sites enhance the ammonia resistance of the catalyst, bolstering its performance in alcohol dehydrogenation and oxygen activation, the key steps in the oxidative cyanation. This investigation demonstrates the high efficiency of a single-site Ru catalyst for nitrile production.
- Gates, Bruce C.,Guan, Erjia,Meng, Xiangju,Wang, Chengtao,Wang, Hai,Wang, Liang,Wang, Sai,Xiao, Feng-Shou,Xu, Dongyang,Xu, Hua,Yang, Bo,Zhang, Jian
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p. 6299 - 6308
(2020/07/21)
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- COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS
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A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.
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Paragraph 00148
(2016/06/14)
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- Synthesis of nitriles from amines using nanoscale Co3O4-based catalysts via sustainable aerobic oxidation
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The selective oxidation of amines for the benign synthesis of nitriles under mild conditions is described. Key to success for this transformation is the application of reusable cobalt oxide-based nanocatalysts. The resulting nitriles constitute key precursors and central intermediates in organic synthesis.
- Natte, Kishore,Jagadeesh, Rajenahally V.,Sharif, Muhammad,Neumann, Helfried,Beller, Matthias
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supporting information
p. 3356 - 3359
(2016/04/09)
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- "Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles
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Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable "nanorust" (nanoscale Fe2O3)-based catalysts applying molecular oxygen.
- Jagadeesh, Rajenahally V.,Junge, Henrik,Beller, Matthias
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- Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
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The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
- An, Xiao-De,Yu, Shouyun
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supporting information
p. 5064 - 5067
(2015/11/03)
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- One-pot oxidative conversion of alcohols into nitriles by using a TEMPO/PhI(OAc)2/NH4OAc system
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A direct conversion of alcohols into nitriles with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source is reported. This transformation, which proceeds through an oxidation-imination-aldimine oxidation sequence in situ, has been applied to a range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols. Highly chemoselective ammoxidation of primary alcohols in the presence of secondary alcohols was also achieved. Georg Thieme Verlag Stuttgart New York.
- Vatèle, Jean-Michel
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p. 1275 - 1278
(2014/06/10)
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- Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst
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An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.
- Sridhar, Madabhushi,Reddy, Mallu Kishore Kumar,Sairam, Vangipuram Venkata,Raveendra, Jillella,Godala, Kondal Reddy,Narsaiah, Chinthala,Ramanaiah, Beeram China,Reddy, Cirandur Suresh
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experimental part
p. 3421 - 3424
(2012/08/08)
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- S,S-dimethyl dithiocarbonate: A useful reagent for efficient conversion of aldoximes to nitriles
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Dimethyl dithiocarbonate (DMDTC) has been shown to be an efficient dehydrating agent for a range of oximes derived from aliphatic, aromatic and heteroaromatic aldehydes yielding the corresponding nitriles in high yields.
- Khan, Taukeer Ahmad,Peruncheralathan, Saravanan,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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p. 2019 - 2021
(2007/10/03)
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- Two-carbons homologation of methyl ketones examplified for the synthesis of citral from 6-methyl-5-hepten-2-one
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New facile syntheses of 3,7-dimethyl-octadien-2,6-al (citral) from homologation of 6-methyl-5-hepten-2-one are reported.
- Valla, Alain,Cartier, Dominique,Laurent, Alain,Valla, Benoist,Labia, Roger,Potier, Pierre
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p. 1195 - 1201
(2007/10/03)
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- A simple and highly efficient one-pot chemoselective synthesis of nitriles from aldehydes: Mechanistic insight and selectivity control through modulation of electronic and steric factors
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Aldehydes are converted into nitriles in a one-pot reaction by treatment with H2NOH·HCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavage (e.g. methoxy, benzyloxy) or aromatic nucleophilic substitution (e.g. nitro or chloro) takes place for substrates beating such functionalities. Electronic and steric factors around the aldehyde carbon affect the rate of nitrile formation. Excellent to moderate selectivity is observed during intermolecular competition between pair of aldehydes with varying electronic and steric requirements.
- Chakraborti,Kaur,Roy
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p. 1000 - 1006
(2007/10/03)
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- A new efficient method for the conversion of aldehydes into nitriles using ammonia and hydrogen peroxide
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Aldehydes were converted into the corresponding nitriles by a homogeneous reaction with ammonia and aqueous hydrogen peroxide in the presence of copper salts or complexes under mild conditions. (C) 2000 Elsevier Science Ltd.
- Erman,Snow,Williams
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p. 6749 - 6752
(2007/10/03)
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- Synthesis and characterization of all-E-(4,4'-13C2)-astaxanthin strategies for labelling the C15-end groups of carotenoids
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The all-E isomer of (4,4'-13C2)astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% 13C enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C15 + C10 + C15 strategy was used. The central C10-synthon, 2,7-dimethylocta-2,4,6-triene- 1,8-dial (3), was coupled with 13C-enriched C15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C15-phosphonium salt.
- Jansen, Frans Jos H. M.,Lugtenburg, Johan
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p. 829 - 836
(2007/10/03)
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- One-pot synthesis of nitriles from aldehydes under microwave irradiation: Influence of the medium and mode of microwave irradiation on product formation
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Chemoselective transformation of aldehyde to nitrile takes place in a one-pot reaction by treatment with H2NOHHCl in N- methyl-2-pyrrolidinone (NMP) under microwave irradiation using convection mode.
- Chakraborti, Asit K.,Kaur, Gurmeet
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p. 13265 - 13268
(2007/10/03)
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