103383-80-8Relevant articles and documents
Metal free one-pot synthesis of α-ketoamides from terminal alkenes
Dutta, Sayan,Kotha, Surya Srinivas,Sekar, Govindasamy
, p. 47265 - 47269 (2015)
A practical approach towards the synthesis of α-ketoamides from readily available terminal alkenes (styrenes) has been developed. Use of inexpensive I2/2-iodoxybenzoic acid (IBX) in dimethyl sulphoxide (DMSO) as an oxidant under metal free one-pot conditions makes this methodology versatile.
Aerobic oxidative amidation of alkynes using titanium oxide encapsulated cuprous iodide nanoparticles (CuI@TiO2)
Dutta, Pratip Kumar,Dhar, Basabbijayi,Sen, Subhabrata
, p. 12062 - 12071 (2018)
A catalyst consisting of titanium oxide encapsulated cuprous iodide nanoparticles was prepared via a sol-gel method using inexpensive raw materials and was harnessed successfully in the oxidative amidation of alkynes via an environmentally benign and sustainable protocol. The mechanism of action of this transformation was thoroughly discussed. The robustness of the catalyst was elucidated by the synthesis of diverse analogues of α-ketoarylamide from a variety of electron rich and poor substrates via a simple procedure in moderate to high yields, with no generation of toxic by-products, in good recyclability up to five cycles, under solvent free and aerobic conditions. The chemical nature, morphology and loading of the CuI@TiO2 nanocatalyst were investigated by TEM, SEM, XPS, EDX, powder XRD, BET, TGA and ICP-MS.
Double carbonylation of iodoarenes in the presence of reusable palladium catalysts immobilised on supported phosphonium ionic liquid phases
Urbán, Béla,Szabó, Péter,Srankó, Dávid,Sáfrán, Gy?rgy,Kollár, László,Skoda-F?ldes, Rita
, p. 195 - 205 (2018)
The first heterogeneous carbonylation reaction carried out with palladium catalysts immobilised on phosphonium ion modified silica supports is reported. The supported ionic liquid phases were characterised by solid state NMR and FT-IR measurements. The presence of the phosphonium ions on the surface made it possible to carry out double carbonylation in apolar toluene efficiently that resulted in reduced metal leaching. The introduction of dicationic moieties on the solid support has been proved to lead to a further increase in catalyst stability. The catalysts were proved to produce α-ketoamide products with excellent selectivity in the carbonylation of iodoarenes with aliphatic amines while monocarbonylation was the only reaction observed with aniline derivatives. The catalysts could be recycled and used in at least 10 subsequent runs under optimised conditions.
Stabilized Cu2O nanoparticles on rGO highly catalyzed direct oxidative coupling synthesis of Α-ketoamides with molecular oxygen
Lu, Weiyang,Sun, Wei,Tan, Xiaofeng,Wang, Bin,Yang, Hua,Gao, Lingfeng,Zheng, Gengxiu
, (2019)
In this study, a green, efficient, recyclable Cu2O nanoparticles on reduced graphene oxide (Cu2O-NPs@rGO) carbon-based composite catalyst was synthesized by facile one-pot hydrothermal method. And Cu2O-NPs@rGO catalyst was
Phosphine-free double carbonylation of iodobenzene in the presence of reusable supported palladium catalysts
Papp, Máté,Skoda-F?ldes, Rita
, p. 193 - 199 (2013)
Various silica supported palladium catalysts were prepared and tested in the double carbonylation of iodobenzene in the presence of secondary amines. The catalysts were proved to produce α-ketoamide products with excellent selectivity in most cases. At the same time, bulky amines hindered double carbonylation and led to the formation of amides as the main products. Under optimal conditions, the catalysts could be recycled at least six times. An increase in the reaction time led to a decrease in the amount of leached palladium.
Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl
Chen, De,Cheng, Chaozhihui,Zeng, Sheng,Luo, Yongyue,Zhang, Jiajia,Deng, Wei,Zeng, Zebing,Wang, Ruijia,Xiang, Jiannan
, (2020)
A novel and efficient method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through C[sbnd]N bond oxidative cleavage and formation a novel C[sbnd]N bond. This reaction system has a broad reaction scope, providing a facile pathway for the α-functionalization of α-amino ketones.
One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
Ma, Jianting,Cui, Xue,Xu, Junyu,Tan, Yinfeng,Wang, Yan,Wang, Xuesong,Li, Youbin
supporting information, p. 3661 - 3667 (2022/02/07)
A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.
Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides
Yang, Shu-Qing,Yao, Yin-Qing,Chen, Xiao-Chao,Lu, Yong,Zhao, Xiao-Li,Liu, Ye
, p. 1032 - 1041 (2021/05/07)
The amino dicarbonylation of aryl halides affording α-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2(MeCN)2 and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and α-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2(MeCN)2-L4 catalytic system favors the amino dicarbonylation toward α-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.
Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature
Junaid, Qazi Mohammad,Kandasamy, Jeyakumar,Popuri, Sureshbabu,Sabiah, Shahulhameed,Singh, Shweta
, p. 7134 - 7140 (2021/08/30)
A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede
