53256-22-7Relevant academic research and scientific papers
Facile synthesis of aziridines from imines and diazoesters or aldehydes, amines, and diazoesters using a catalytic amount of lanthanide triflate
Nagayama, Satoshi,Kobayashi, Shu
, p. 685 - 686 (1998)
In the presence of a catalytic amount of lanthanide triflate (Ln(OTf)3), imines reacted with ethyl diazoester in hexane at room temperature to afford the corresponding aziridines in high yields with high diastereoselectivities. Based on these r
Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines
Chen, Zhiwei,Shi, Guang,Tang, Wei,Sun, Jie,Wang, Wenxing
supporting information, p. 951 - 955 (2021/02/03)
A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.
Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution
Lei, Tao,Liang, Ge,Cheng, Yuan-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 5385 - 5389 (2020/07/08)
Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.
Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
Cai, Yichao,Chen, Chunxia,Chen, Xin,Liu, Yajie,Peng, Jinsong,Song, Zirui,Sun, Peng,Yang, Jiaojiao
, p. 75 - 84 (2019/12/26)
Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The i
Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes
Benítez-Puebla, Luis J.,López, Julio,Flores-álamo, Marcos,Cruz, David Cruz,Pe?a-Cabrera, Eduardo,Delgado, Francisco,Tamariz, Joaquín,Vázquez, Miguel A.
, p. 6571 - 6578 (2019/10/22)
The results of a study of the reactivities of alkynyl Fischer carbenes in the syntheses of diazaborinine derivatives 7a-i are reported. The strategy employed included the use of β-amino-α,β-unsaturated carbenes (3a–j) with different amines in order to determine the scope of a previously unknown catalytic reaction in the presence of copper salts and anilines. The reaction was highly stereoselective, yielding (Z)-isomers of the β-amino-1-azadiene framework as the main products (4a–o). As an extension of this research, the compounds 4a–o proved to be suitable precursors for the syntheses of diazaborinine scaffolds in good yields (7a-i).
Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols
Dong, Mengxian,Wang, Jie,Wu, Shijie,Zhao, Yang,Ma, Yangyang,Xing, Yongfei,Cao, Fei,Li, Longfei,Li, Zhenqiu,Zhu, Huajie
supporting information, p. 4602 - 4610 (2019/08/30)
Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).
Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 6452 - 6456 (2019/09/06)
Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
Isobutyl Nitrite-Mediated Synthesis of Quinoxalines through Double C?H Bond Amination of N-Aryl Enamines
Jiao, Yan-Xiao,Wei, Lin-Su,Zhao, Chun-Yang,Wei, Kai,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
, p. 4446 - 4451 (2018/10/20)
An efficient and metal-free double C?H bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β-imino oxime ester intermediate. A quinoxaline derivative could be prepared from β-carbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps. (Figure presented.).
PIDA/TBAB-Promoted Oxidative Geminal Dibromofunctionalization of Alkynes: Direct Synthesis of Geminal Diazides
Arepally, Sagar,Babu, Venkata Nagarjuna,Polu, Ashok,Sharada, Duddu S.
supporting information, p. 5700 - 5705 (2018/10/15)
PIDA/TBAB-promoted oxidative geminal diazidofunctionalization of alkynes has been described for the first time. The transformation demonstrates a mechanistically distinctive approach to access geminal diazides, in which TBAB plays a crucial role as brominating agent and for the in situ generation of tetrabutylammonium azide. Furthermore, we have demonstrated here the first cycloaminative strategy by tactically employing the two azides groups leading to quinoxalines and synthesis of bis-triazole derivatives via copper catalysis.
A sustainable synthesis of 2-aryl-3-carboxylate indolines from N-aryl enamines under visible light irradiation
Wu, Cheng-Juan,Cao, Wen-Xiao,Lei, Tao,Li, Zhi-Hua,Meng, Qing-Yuan,Yang, Xiu-Long,Chen, Bin,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 8320 - 8323 (2017/07/26)
With visible light irradiation of a catalytic amount of Ir(ppy)3 at room temperature, a number of N-aryl enamines were transformed into their corresponding indoline products in good to excellent yields without requiring any extra additives. This is the first example of the synthesis of indolines via the intramolecular cyclization of enamines under visible light irradiation.
