- Direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2
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This paper described a mild and efficient direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good to excellent yield. Chiral amino acids derivatives were transformed into amides without racemization in moderate yield. The possible mechanism of direct amidation catalyzed by TiCp2Cl2 was discussed. This catalytic method is very suitable for the amidation of low sterically hindered arylacetic acid, fatty acids with different low sterically hindered amines except aniline, as well as the amidation of aryl formic acid with benzyl and aliphatic amines.
- Wang, Hui,Dong, Wei,Hou, Zhipeng,Cheng, Lidan,Li, Xiufen,Huang, Longjiang
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- Solvent-Free N-Alkylation of Amides with Alcohols Catalyzed by Nickel on Silica–Alumina
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The N-alkylation of phenylacetamide with benzyl alcohol has been studied using Ni/SiO2–Al2O3. In the optimized conditions, the desired product was isolated in an excellent 98 % yield. The reaction could advantageously be performed in neat conditions, with a slight excess of amide and a catalytic amount of base. These conditions were tested on a large range of amides and alcohols, affording 24 compounds in 13 to 99 % isolated yields.
- Charvieux, Aubin,Le Moigne, Louis,Borrego, Lorenzo G.,Duguet, Nicolas,Métay, Estelle
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supporting information
p. 6842 - 6846
(2019/11/11)
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- Triphenyl borate catalyzed synthesis of amides from carboxylic acids and amines
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Herein we report triphenyl borate as a new catalyst for synthesis of amides by catalytic condensation of carboxylic acids and amines. Our protocol is applicable for synthesis of wide range of amides furnishing excellent yields up to 92%. In addition developed method requires low catalyst loading, short time, less amount of solvent, works under air atmosphere and notably no need of azeotropic reflux using special Dean Stark apparatus or molecular sieves.
- Ghorpade, Seema A.,Sawant, Dinesh N.,Sekar, Nagaiyan
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supporting information
p. 6954 - 6958
(2018/10/24)
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- Hafnium-catalyzed direct amide formation at room temperature
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Herein, the first example of a metal-catalyzed protocol for direct amidation of nonactivated carboxylic acids at ambient temperature (26 °C) is presented. The mild reaction conditions give rise to high yields of a range of amides in reaction times as short as 90 min, employing a commercial hafnium complex, [Hf(Cp)2Cl2], as catalyst. Amino acids are transformed into their corresponding amides without racemization, and the catalyst displays full selectivity for the amidation of carboxylic acids over esters. Electronic properties of the carboxylic acids were found to have a strong influence on the rate of the amidation reaction, and the need for a balanced amount of molecular sieves was observed to be highly important for optimal reaction outcome.
- Lundberg, Helena,Adolfsson, Hans
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p. 3271 - 3277
(2015/06/16)
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- Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
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A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
- Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
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supporting information
p. 3683 - 3690
(2014/05/20)
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- Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines
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An efficient aminocarbonylation of N-tosylhydrazones derived from aromatic aldehydes and ketones mediated by molybdenum hexacarbonyl is reported. This method is palladium-free and provides a rapid access to the α-aryl acetamides in moderate to good yields.
- Rao, K. Penta,Basak, Ashok K.,Raju, Amancha,Patil, Vikas S.,Reddy, L. Krishnakanth
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p. 5510 - 5513
(2013/09/23)
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- Microwave specific Wolff rearrangement of α-diazoketones and its relevance to the nonthermal and thermal effect
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α-Diazoketones possess high electric dipole moments, as a consequence of the dipolar nature of the diazocarbonyl functional group. The vectorial analysis, theoretical calculations (PM3 and ab initio), and literature reports based on experimental and theor
- Sudrik, Surendra G.,Chavan, Sambhaji P.,Chandrakumar,Pal, Sourav,Date, Sadgopal K.,Chavan, Subhash P.,Sonawane, Harikisan R.
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p. 1574 - 1579
(2007/10/03)
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- Potential Central Nervous System Active Agents. 1. Synthesis of N-Benzylphenylacetamides
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Six N-benzylphenylacetamides variously substituted on the acyl part with chloro, methyl, or methoxyl groups, including five new ones, were synthesized by heating their corresponding N-benzylammonium salts in o-xylene.Their IR, NMR, and mass-spectral (MS) data are presented and compared with those of the N-benzylbenzamides and N-benzylacetamide, respectively.
- Agwada, Vincent C.
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p. 481 - 483
(2007/10/02)
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