- N,N-dimethylamination of acid chlorides with DMF
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A solution of acid chlorides 3a-g in DMF solvent was refluxed to give N,N-dimethylamides 4a-f and 5g in excellent yields.
- Woo Song Lee,Ki Hun Park,Yoon
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- Ruthenium hydride/nitrogen tridentate ligand-catalyzed α-alkylation of acetamides with primary alcohols
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The α-alkylation reaction of acetamides with primary alcohols to afford the corresponding amides was accomplished effectively using RuHCl(CO)(PPh3)3 as a catalyst, nitrogen tridentate ligand L1 as an additive, and KOtBu as a base. While the addition of bpy was effective only for benzylic alcohols, L1 affected the alkylation reaction when both benzylic and non-benzylic type alcohols were used.
- Kuwahara, Takashi,Fukuyama, Takahide,Ryu, Ilhyong
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- 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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- Manganese-catalyzed direct C-C coupling of α-C-H bonds of amides and esters with alcohols: Via hydrogen autotransfer
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Herein we report an efficient manganese-catalyzed C-alkylation of unactivated amides and tert-butyl acetate using alcohols as alkylating agents. This elegant approach exhibits a broad substrate scope providing the C-C coupled products of amides via a hydrogen auto-transfer strategy using aryl, heteroaryl, and aliphatic alcohols.
- Rana, Jagannath,Gupta, Virendrakumar,Balaraman, Ekambaram
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supporting information
p. 7094 - 7099
(2019/06/06)
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- Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis
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The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.
- Jang, Yoon Kyung,Krückel, Tobias,Rueping, Magnus,El-Sepelgy, Osama
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supporting information
p. 7779 - 7783
(2018/12/14)
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- Supported Gold Nanoparticles for Efficient α-Oxygenation of Secondary and Tertiary Amines into Amides
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Although the α-oxygenation of amines is a highly attractive method for the synthesis of amides, efficient catalysts suited to a wide range of secondary and tertiary alkyl amines using O2as the terminal oxidant have no precedent. This report describes a novel, green α-oxygenation of a wide range of linear and cyclic secondary and tertiary amines mediated by gold nanoparticles supported on alumina (Au/Al2O3). The observed catalysis was truly heterogeneous, and the catalyst could be reused. The present α-oxygenation utilizes O2as the terminal oxidant and water as the oxygen atom source of amides. The method generates water as the only theoretical by-product, which highlights the environmentally benign nature of the present reaction. Additionally, the present α-oxygenation provides a convenient method for the synthesis of18O-labeled amides using H218O as the oxygen source.
- Jin, Xiongjie,Kataoka, Kengo,Yatabe, Takafumi,Yamaguchi, Kazuya,Mizuno, Noritaka
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supporting information
p. 7212 - 7217
(2016/07/06)
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- General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
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The borrowing hydrogen or hydrogen autotransfer methodology is an elegant and sustainable or green concept to construct carbon-carbon bonds. In this concept, alcohols, which can be obtained from barely used and indigestible biomass, such as lignocellulose, are employed as alkylating reagents. An especially challenging alkylation is that of unactivated esters and amides. Only noble metal catalysts based on iridium and ruthenium have been used to accomplish these reactions. Herein, we report on the first base metal-catalyzed α-alkylation of unactivated amides and esters by alcohols. Cobalt complexes stabilized with pincer ligands, recently developed in our laboratory, catalyze these reactions very efficiently. The precatalysts can be synthesized easily from commercially available starting materials on a multigram scale and are self-activating under the basic reaction conditions. This Co catalyst class is also able to mediate alkylation reactions of both esters and amides. In addition, we apply the methodology to synthesize ketones and to convert alcohols into aldehydes elongated by two carbon atoms.
- Deibl, Nicklas,Kempe, Rhett
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supporting information
p. 10786 - 10789
(2016/09/09)
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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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- Copper-catalyzed amide bond formation from formamides and carboxylic acids
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A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.
- Liu, Hong-Qiang,Liu, Jun,Zhang, Yang-Hui,Shao, Chang-Dong,Yu, Jing-Xun
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- PROCESS FOR PRODUCING N,N-DIALKYL SUBSTITUTED FATTY ACIDS AMIDES
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Disclosed herein is a process for producing Dialkyl substituted fatty acids amides. More particularly the present invention provides a process for producing pure form of N,N-dimethylamide of aliphatic carboxylic acids, wherein the aliphatic carboxylic acid is Octanoic Acid and Hexanoic Acid. The disclosed process comprises condensing Alkanoyl Chloride with dilute solution of Dialkylamine at a temperature of about 8 to 12°C and isolating the crude by salting out the reaction mixture employing Sodium Chloride and distilling the same under vacuum.
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Page/Page column 6
(2008/06/13)
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- Water insoluble composition of an aldoxime extractant and an equilibrium modifier
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Alternative equilibrium modifiers for use with aldoxime extractants, such as hydroxyl aryl aldoxime extractants, employed in the process for extraction of metal values, particularly copper values, in the extraction from aqueous solutions, in which the extractant and modifiers are employed in an organic solvent phase, the solvent being a water insoluble, water immiscible hydrocarbon solvent, such as a kerosene.
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- Tin-free reductive photochemical carboxymethylation of olefins with α- alkylthioacetates
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An efficient tin-free reductive photochemical carboxymethylation of olefins with α-alkylthioacetates is developed, which (a) is an experimentally simple technique furnishing substituted derivatives of fatty acids in moderate to good yields, (b) is compatible with polar/protic functional groups and solvents, (c) does not require a special reducing reagent, (d) is fairly insensitive to the presence of dissolved oxygen and, generally, does not require degassing prior to irradiation. The critical feature of the mechanism is the 'reluctance' of short-lived MeS' to group- transfer, resulting in hydrogen abstraction from the media.
- Deng, Lisa X.,Kutateladze, Andrei G.
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p. 7829 - 7832
(2007/10/03)
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- STEREOCONTROLLED IODOLACTONIZATION OF ERYTHRO AND THREO TERTIARY AMIDES
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A series of α-mono and dialkyl-β-oxygenated (hydroxyl and alkyl ester) teriary amides were subjected to iodolactonization and it was observed that with only 1 exception, (threo 11b), all of the compounds cyclized with useful levels of stereoselection (at least 3:1).While the origin of this effect is obscure, these results suggest that in such amide substrates with at least one substituent larger than methyl a to the amide, iodolactonization is a viable strategy for the stereocontrolled preparation of highly substituted γ-butyrolactones.
- Rotella, David P.,Li, Xun
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p. 1205 - 1211
(2007/10/02)
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