- Palladium Catalyzed Aminocarbonylation of Benzylic Ammonium Triflates with Nitroarenes: Synthesis of Phenylacetamides
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A palladium catalyzed reductive aminocarbonylation of benzylic ammonium triflates with nitroarenes for the synthesis of phenylacetamides was developed. Using Pd(acac)2/DPPF catalyst system, a range of different substituted phenylacetamides were prepared in moderate to good yields from benzylic ammonium triflates and nitroarenes through Csp3?N bond cleavage. A variety of alkyl, aryl, and halide substituents on both substrates can be used, and many useful functional groups can be tolerated. (Figure presented.).
- Yang, Li-Miao,Li, Shan-Shan,Zhang, You-Ya,Lu, Jin-Liang,Deng, Jing-Tong,Ma, Ai-Jun,Zhang, Xiang-Zhi,Zhang, Shu-Yu,Peng, Jin-Bao
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supporting information
p. 2061 - 2065
(2021/02/26)
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- Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
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An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
- Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
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supporting information
p. 3099 - 3103
(2018/05/22)
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- Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation
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The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.
- T?th, Balázs L.,Kovács, Szabolcs,Sályi, Gerg?,Novák, Zoltán
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supporting information
p. 1988 - 1992
(2016/02/18)
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- Metal-free hydration of ynamides: Convenient approach to amides
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The trifluoroacetic acid (TFA) mediated hydration of ynamides was developed, which is an efficient approach for the synthesis of N-monosubstituted amides. This convenient method is effective with a wide range of substrates under room temperature condition, and the products are obtained in high to excellent yields through an easy work-up process.
- Huang, Hai,Tang, Luning,Xi, Yang,He, Guangke,Zhu, Hongjun
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supporting information
p. 1873 - 1876
(2016/04/19)
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- A simple and greener approach for the amide bond formation employing FeCl3 as a catalyst
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Catalytic use of FeCl3 in the presence of glacial AcOH for the direct amidation of acid with amine in toluene has been described in this paper. The protocol worked well for the less nucleophilic aniline and its variants which gave the best results under the present reaction conditions. Amidation of bromoacetic acid and sterically hindered amino acid also proceed effectively to yield the corresponding amides. The protocol is catalytic and circumvents the use of stoichiometric amounts of reagents. The reaction led to water soluble by-products and thus makes the product isolation easier.
- Basavaprabhu,Muniyappa, Krishnamurthy,Panguluri, Nageswara Rao,Veladi, Panduranga,Sureshbabu, Vommina V.
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supporting information
p. 7746 - 7749
(2015/10/12)
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- Chemoselective Reductive Deoxygenation and Reduction of α-Keto Amides by using a Palladium Catalyst
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A palladium catalyst is used to synthesize 2,N-diphenylacetamides and α-hydroxy amides from readily available α-keto amides by chemoselective reductive deoxygenation and chemoselective reduction using polymethylhydrosiloxane (PMHS). This methodology has t
- Mamillapalli, N. Chary,Sekar, Govindasamy
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p. 3273 - 3283
(2015/11/03)
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- Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation
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2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.
- Rajan
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p. 287 - 291
(2015/01/30)
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- Nitrogen enriched mesoporous organic polymer anchored copper(ii) material: An efficient and reusable catalyst for the synthesis of esters and amides from aromatic systems
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A new copper-grafted mesoporous poly-melamine-formaldehyde (Cu-mPMF) has been synthesized from melamine and paraformaldehyde in DMSO medium, followed by grafting of Cu(ii) at its surface. Cu-mPMF has been characterized by elemental analysis, powder XRD, HR TEM, FE-SEM, N2 adsorption study, FT-IR, UV-vis DRS, TGA-DTA, EPR spectroscopy, Raman spectroscopy and X-ray photoelectron spectroscopy (XPS). The Cu-grafted mesoporous material showed very good catalytic activity in methyl esterification of benzylic alcohols and amidation of nitriles. Moreover, the catalyst is easily recoverable and can be reused seven times without appreciable loss of catalytic activity in the above reactions. The highly dispersed and strongly bound Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-mPMF catalyst. Due to strong binding with the functional groups of the polymer, no evidence of leached copper from the catalyst during the course of reaction emerged, suggesting true heterogeneity in the catalytic process. This journal is
- Molla, Rostam Ali,Iqubal, Md. Asif,Ghosh, Kajari,Kamaluddin,Islam, Sk. Manirul
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p. 6546 - 6559
(2015/04/14)
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- Carboxyl activation of 3-mercapto-5,6-diphenyl-1,2,4-triazine through N-phenylacetyl-5,6-diphenyl-1,2,4-triazine-3-thione
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The carboxyl activation ability of 3-mercapto-5,6-diphenyl-1,2,4-triazine has been established by coverting it into N-phenylacetyl-5,6-diphenyl-1,2,4-triazine-3-thione and this was then subjected to aminolysis and esterification with amines and alcohols respectively and selective aminolysis with aminoalcohols-monitoring chemically and confirmed spectrophotometrically by UV-Visible scannings. It could be proved that 3- mercapto-5,6-diphenyl-1,2,4-triazine is an efficient carboxyl activating group which can be successfully applied in solid phase peptide synthesis.
- Rajan
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p. 119 - 126
(2019/01/21)
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- An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and amines in water
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The reactions between nitriles and amines catalyzed by Cu(OAc)2 and 2-piperidinecarboxylic acid were carried out in pure water without any other additives. A variety of substituted amides can be obtained in moderate to good yields up to 90%.
- Li, Xiaoya,Li, Zhengkai,Deng, Hang,Zhou, Xiangge
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supporting information
p. 2212 - 2216
(2013/05/09)
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- A straightforward synthesis of N-monosubstituted α-keto amides via aerobic benzylic oxidation of amides
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An efficient sodium bicarbonate promoted aerobic oxidation reaction to prepare N-monosubstituted α-keto amides in the presence of n-tetrabutylammonium hydrogensulfate (TBAHS) was described. This reaction provides a very simple and convenient synthetic route to N-monosubstituted α-keto amides from easily available aryl- or heteroarylacetamides in good to high yields without using toxic reagents and harsh conditions.
- Shao, Jun,Huang, Xiaomei,Wang, Siyuan,Liu, Bingxin,Xu, Bin
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supporting information; experimental part
p. 573 - 579
(2012/01/13)
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- Lithiation of N-(2-Alkylphenyl)alkanamides and Related Compounds. A Modified Madelung Indole Synthesis
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A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.
- Houlihan, William J.,Parrino, Vincent A.,Uike, Yasuyuki
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p. 4511 - 4515
(2007/10/02)
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