- METHOD FOR PRODUCING AMIDE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method whereby, while using a catalyst that contains a transition metal and can be relatively easily synthesized, even with a small amount of the transition metal, an amide compound can be produce efficiently by the α-alkylation of the amide compound. SOLUTION: A method for producing an amide compound includes the step of: causing a primary alcohol compound and an amide compound to react with each other in a reaction liquid containing a transition metal nanoparticle (M-NPs) of at least one of a ruthenium nanoparticle or an iridium nanoparticle, and a base, to produce an amide compound. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0030; 0033-0037; 0044-0045
(2021/09/17)
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- Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines
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Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.
- An, Duk Keun,Jaladi, Ashok Kumar,Kim, Hyun Tae,Yi, Jaeeun
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supporting information
(2021/11/17)
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- Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation
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A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.
- Fuentes de Arriba, ángel L.,Lenci, Elena,Sonawane, Mahendra,Formery, Odilon,Dixon, Darren J.
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supporting information
p. 3655 - 3659
(2017/03/21)
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- A highly efficient catalytic α-alkylation of unactivated amides using primary alcohols
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The α-alkylation of unactivated amides with alcohols is described. Using a NCP-type pincer Ir complex as the precatalyst and KOtBu as the base, the reactions of secondary or tertiary acetamides with benzyl or nonbenzyl primary alcohols occur at 80 °C, furnishing the alkylation products in good yields. This method represents a practical and green means of α-alkylation of amides in a relatively mild, efficient, and selective manner with low catalyst loadings (0.5 mol %).
- Yao, Wubing,Ma, Xiaochen,Guo, Le,Jia, Xiangqing,Hu, Aiguo,Huang, Zheng
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supporting information
p. 2919 - 2921
(2016/06/13)
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- Ruthenium-catalyzed direct α-alkylation of amides using alcohols
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The highly efficient direct α-alkylation of unactivated amides has been accomplished using alcohols in the presence of the Ru-PNN catalyst (0.1 mol%) with a high turnover number. Using this approach, 2-oxindole was directly transformed into C3-alkylated 3-hydroxyindolin-2-one in one step without the use of any oxidant.
- Chaudhari, Moreshwar Bhagwan,Bisht, Girish Singh,Kumari, Pooja,Gnanaprakasam, Boopathy
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supporting information
p. 9215 - 9220
(2016/10/13)
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- Iridium-catalyzed selective α-alkylation of unactivated amides with primary alcohols
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The first α-alkylation of unactivated amides with primary alcohols is described. An effective and robust iridium pincer complex has been developed for selective α-alkylation of tertiary and secondary acetamides involving a borrowing hydrogen methodology. The method is compatible with alcohols bearing various functional groups. This presents a convenient and environmentally benign protocol for α-alkylation of amides.
- Guo, Le,Liu, Yinghua,Yao, Wubing,Leng, Xuebing,Huang, Zheng
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supporting information
p. 1144 - 1147
(2013/04/10)
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- Copper-catalyzed oxidative coupling of carboxylic acids with N,N-dialkylformamides: An approach to the synthesis of amides
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A new synthetic approach for amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. A new synthetic approach to amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst and aqueous tert-butyl hydroperoxide (TBHP) as a sacrificial oxidant. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. Copyright
- Kumar, P. Santhosh,Kumar, G. Sathish,Kumar, R. Arun,Reddy, N. Veera,Rajender Reddy
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supporting information
p. 1218 - 1222
(2013/04/10)
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- Method For Producing Amides In The Presence Of Superheated Water
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The invention relates to a method for producing carboxylic acid amides, according to which at least one carboxylic acid of formula (I) [in-line-formulae]R3—COON ??(I)[/in-line-formulae] wherein R3 is hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 50 carbon atoms, is reacted with at least one amine of formula (II) [in-line-formulae]HNR1R2 ??(II)[/in-line-formulae] wherein R1 and R2 are independently hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is reacted in the presence of superheated water, under microwave irradiation, to form a carboxylic acid amide.
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Page/Page column 9
(2011/05/03)
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- Functional group-selective poisoning of molecular catalysts: A ruthenium cluster-catalysed highly amide-selective silane reduction that does not affect ketones or esters
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The addition of amines eliminates the catalytic activity of a triruthenium cluster in the hydrosilane reduction of ketones and esters without affecting the rate of reduction of amides; selective reduction of the amide group in amido ketones and amido esters is accomplished. The Royal Society of Chemistry.
- Sasakuma, Hidehiro,Motoyama, Yukihiro,Nagashima, Hideo
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p. 4916 - 4918
(2008/09/17)
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- Product selectivity in the electroreduction of thioesters
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The electroreduction of differently substituted aromatic and aliphatic thioesters (RCOSR′) led to regioselective reactions depending on the nature of the substituents. Thus, the cleavage between the carbonyl group and the SR′ group afforded α-diketones an
- We?wer,Olivero,Du?ach
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p. 1709 - 1714
(2007/10/03)
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- Concentration of hydrophobic organic compounds and extraction of protein using alkylammoniosulfate zwitterionic surfactant mediated phase separations (cloud point extractions)
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The zwitterionic surfactants 3-[nonyl- (or decyl-) dimethylammonio]propyl sulfate, (C9-APSO4 or C10-APSO4) were synthesized using Nilsson's procedure, and their phase separation behavior under different experimental conditions was evaluated. The results indicate that such zwitterionic surfactants can be utilized for the extraction/preconcentration of hydrophobic species in a manner akin to that previously reported for nonionic surfactants. This was demonstrated for several practical applications including the extraction/preconcentration of some steroidal hormones and vitamin E prior to high-performance liquid chromatography analysis. The zwitterionic surfactant mediated phase separation was also applied to the extraction of the hydrophobic membrane protein, bacterio-rhodopsin, from the hydrophilic cytochrome c protein, both originally present In an aqueous phase. The concentration factors for this aqueous two-phase extraction technique using C10-APSO4 ranged from 26 to 35 with recoveries In the range 88 to > 96%. Some comparative studies Indicate that the use of zwittterionic surfactants In lieu of nonionic surfactants (e.g. polyoxyethylene(7.5) nonyl phenyl ether PONPE-7.5) In such an extraction method offers some significant advantages such as purer, homogeneous surfactant preparation, minimum background absorbance at UV detection wavelengths, the two-phase region occurring at lower temperatures, and greater extraction efficiencies/concentration factors among others.
- Saitoh, Tohru,Hinze, Willie L.
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p. 2520 - 2525
(2007/10/02)
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