69838-98-8Relevant academic research and scientific papers
Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination
Gao, Pengpeng,Zhang, Xiaohui,Zheng, Qing-Zhong
supporting information, p. 10332 - 10336 (2021/12/17)
An efficient inexpensive cobalt(iii)-catalyzed intermolecular amidation of N,N-dialkyl thiobenzamides with 1,4,2-dioxazol-5-ones via C-H bond activation is described. The reaction proceeds with high functional group tolerance under external oxidant free conditions, providing a straightforward approach for the direct modification of thioamide derivatives, which are prevalent organic motifs found in vital biological and pharmaceutical molecules. This journal is
Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites
Bian, Fengxia,Cheng, Hongmei,Jiang, Heyan,Sun, Bin,Tan, Jiangwei,Zang, Cuicui
, p. 279 - 287 (2021/08/21)
Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.
Visible-Light-Mediated Oxidative Amidation of Aldehydes by Using Magnetic CdS Quantum Dots as a Photocatalyst
Xu, Ling,Zhang, Shuai-Zheng,Li, Wei,Zhang, Zhan-Hui
, p. 5483 - 5491 (2021/03/01)
A magnetic CdS quantum dot (Fe3O4/polydopamine (PDA)/CdS) was synthesized through a facile and convenient method from inexpensive starting materials. Characterization of the prepared catalyst was performed by means of FTIR spectrosco
Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative
Hassan Tolba, Amal,Krupi?ka, Martin,Chudoba, Josef,Cibulka, Radek
supporting information, p. 6825 - 6830 (2021/09/11)
We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.
Visible-Light-Driven C-N Bond Formation by a Hexanickel Cluster Substituted Polyoxometalate-Based Photocatalyst
Chang, Jiangnan,Han, Qiuxia,Jiao, Jiachen,Li, Jie,Li, Mingxue
, p. 10022 - 10029 (2021/07/19)
A powerful and attractive route to develop novel photocatalysts for C-N bond formation involves the use of pyrrolidine as the substrate and cocatalyst simultaneously. Herein, a new polyoxometalate (POM)-based metal-organic framework, namely, [Ni6(OH)3(H2O
Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF
Zhang, Jin,Liu, Ying,Jia, Qiangqiang,Wang, Yue,Ma, Yangmin,Szostak, Michal
supporting information, p. 6884 - 6890 (2020/09/15)
We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.
The Hofmann reaction involving annulation of: O -(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6 H -pyrido[1,2- c] quinazolin-6-one derivatives
Gao, Wenjing,Liu, Tongxin,Wan, Yameng,Wu, Hao,Zhang, Guisheng,Zhang, Zhiguo
supporting information, p. 7955 - 7961 (2020/11/30)
A highly efficient PIFA-mediated Hofmann reaction of o-(pyridin-2-yl)aryl amides has been developed to selectively and rapidly construct various potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives. The use of a nontoxic and ec
Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)
Bode, Jeffrey W.,Ryan, Sarah J.,Schuhmacher, Anne,Shiro, Tomoya
, p. 7609 - 7614 (2020/08/14)
Although highly effective for most amide syntheses, the activation of carboxylic acids requires the use of problematic coupling reagents and is often poorly suited for challenging cases such as N-methyl amino acids. As an alternative to both secondary and tertiary amides, we report their convenient synthesis by the rapid oxidation of trifluoroborate iminiums (TIMs). TIMs are easily prepared by acid-promoted condensation of potassium acyltrifluoroborates (KATs) and amines and are cleanly and rapidly oxidized to amides with hydrogen peroxide. The overall transformation can be conducted either as a one-pot procedure or via isolation of the TIM. The unique nature of the neutral, zwitterionic TIMs makes possible the preparation of tertiary amides via an iminium species that would not be accessible from other carbonyl derivatives and can be conducted in the presence of unprotected functional groups including acids, alcohols and thioethers. In preliminary studies, this approach was applied to the late-stage modifications of long peptides and the iterative synthesis of short, N-methylated peptides without the need for coupling agents.
A practical catalytic reductive amination of carboxylic acids
Andrews, Keith G.,Denton, Ross M.,Hirst, David J.,Stoll, Emma L.,Tongue, Thomas,Valette, Damien
, p. 9494 - 9500 (2020/10/02)
We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.
Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent
Mejía-Farfán, Itzel,Solís-Hernández, Manuel,Navarro-Santos, Pedro,Contreras-Celedón, Claudia A.,Cortés-García, Carlos Jesus,Chacón-García, Luis
, p. 18265 - 18270 (2019/07/03)
An efficient transition-metal-based heterogeneous catalyst free procedure for obtaining the oxidative amidation of benzaldehyde using quinones as oxidizing agents in low molar proportions is described here. Pyrrolylquinones (PQ) proved to be more suitable
