16618-52-3Relevant academic research and scientific papers
Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction
Li, Huaifeng,Gon?alves, Théo P.,Zhao, Qianyi,Gong, Dirong,Lai, Zhiping,Wang, Zhixiang,Zheng, Junrong,Huang, Kuo-Wei
, p. 11395 - 11398 (2018)
A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.
Zinc Hydride Catalyzed Chemoselective Hydroboration of Isocyanates: Amide Bond Formation and C=O Bond Cleavage
Sahoo, Rajata Kumar,Sarkar, Nabin,Nembenna, Sharanappa
, p. 11991 - 12000 (2021)
Herein, a remarkable conjugated bis-guanidinate (CBG) supported zinc hydride, [{LZnH}2; L={(ArHN)(ArN)?C=N?C=(NAr)(NHAr); Ar=2,6-Et2-C6H3}] (I) catalyzed partial reduction of heteroallenes via hydroboration is r
A Catalyst-Free Process for the Direct Oxidative Synthesis of Form-anilides from Arylamines and Aldehydes under Air Atmosphere
Qin, Yuancheng,Cheng, Yuanyuan,Luo, Xubiao,Li, Mingjun,Xie, Yu,Gao, Yunhua
, p. 1900 - 1904 (2015)
An efficient and catalyst-free process for the direct oxidative synthesis of formanilides from primary aromatic amines and aliphatic aldehydes has been developed under mild aerobic oxidation conditions. The isotope-labeling experiments indicated that the oxygen atom of the formanilide originated from dioxygen.
Copper-Catalyzed Cascade N-Dealkylation/N-Methyl Oxidation of Aromatic Amines by Using TEMPO and Oxygen as Oxidants
Li, Dianjun,Wang, Shihaozhi,Yang, Jiale,Yang, Jinhui
supporting information, p. 6768 - 6772 (2021/12/31)
A novel tandem N-dealkylation and N-methyl aerobic oxidation of tertiary aromatic amines to N-arylformamides using copper and TEMPO has been developed. This methodology suggested an alternative synthetic route from N-methylarylamines to N-arylformamides.
A NHC-silyliumylidene cation for catalytic N?formylation of amines using carbon dioxide
Leong, Bi-Xiang,Teo, Yeow-Chuan,Condamines, Cloe,Yang, Ming-Chung,Su, Ming-Der,So, Cheuk-Wai
, p. 14824 - 14833 (2020/12/21)
This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2), to catalyze the chemoselective N-formylation of primary and secondary amines using CO2 and PhSiH3 under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h?1; secondary amines, average yield: 98%, average TOF: 17 h?1). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C?N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO2, PhSiH3, and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.
Efficient: N -formylation of primary aromatic amines using novel solid acid magnetic nanocatalyst
Agarwal, Alka,Awasthi, Satish K.,Yadav, Jitendra Kumar,Yadav, Priyanka
, p. 41229 - 41236 (2020/11/23)
Sulfonic acid functionalized over biguanidine fabricated silica-coated heterogeneous magnetic nanoparticles (NP?SO3H) have been synthesized, well characterized and explored for the first time, as an efficient and recyclable catalyst for N-formylation of primary amines under mild reaction conditions. Exploiting the magnetic nature of Fe3O4, the prepared catalyst was readily recovered from the reaction mixture via an external magnet. The catalyst can be reused for up to six cycles without any substantial loss of catalytic activity. The cost effectiveness, simple methodology, wide substrate tolerance, excellent yield and easy work-up are the additional advantages of present catalytic system. This journal is
An efficient method for the N-formylation of amines under catalyst- and additive-free conditions
Xu, Zhuo-Wei,Xu, Wen-Yi,Pei, Xiao-Jun,Tang, Fei,Feng, Yi-Si
supporting information, p. 1254 - 1258 (2019/04/10)
A simple catalyst- and additive-free method for the N-formylation of amines has been developed. The advantages of this protocol include a wide range of functional group tolerance, high efficiency and a lack of required extra promoters under mild conditions. This convenient strategy will provide a facile synthesis towards N-formamide natural products and pharmaceutical derivatives. A mechanism that involves difluorocarbene is proposed for this reaction.
Delineation of the Critical Parameters of Salt Catalysts in the N-Formylation of Amines with CO2
Hulla, Martin,Ortiz, Daniel,Katsyuba, Sergey,Vasilyev, Dmitry,Dyson, Paul J.
supporting information, p. 11074 - 11079 (2019/07/17)
N-formylation of amines combining CO2 as a C1 source with a hydrosilane reducing agent is a convenient route for the synthesis of N-formylated compounds. A large number of salts including ionic liquids (ILs) have been shown to efficiently catalyze the reaction and, yet, the key features of the catalyst remain unclear and the best salt catalysts for the reaction remain unknown. Here we demonstrate the detrimental effect of ion pairing on the catalytic activity and illustrate ways in which the strength of the interaction between the ions can be reduced to enhance interactions and, hence, reactivity with the substrates. In contrast to the current hypothesis, we also show that salt catalysts are more active as bases rather than nucleophiles and identify the pKa where the nucleophilic role of the catalyst switches to the more active basic role. The identification of these critical parameters allows the optimum salt catalyst and conditions for an N-formylation reaction to be predicted.
Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines
Tran, Cong Chi,Kawaguchi, Shin-Ichi,Kobiki, Yohsuke,Matsubara, Hitomi,Tran, Dat Phuc,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
, p. 11741 - 11751 (2019/10/02)
Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.
Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines
Yuan, Yao,Dong, Wu-Heng,Gao, Xiao-Shuang,Xie, Xiao-Min,Zhang, Zhao-Guo
supporting information, p. 11900 - 11903 (2019/10/11)
A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.
