35401-49-1Relevant academic research and scientific papers
Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions
Bian, Yunyun,Chen, Chunxia,Chen, Xin,Mo, Baichuan,Peng, Jinsong,Sun, Peng
, p. 24830 - 24839 (2020/07/14)
Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan-Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan-Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)2/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO4 and KHCO3. Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. This journal is
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
Synthesis of Functionalized Imidazolium Salts via Iodine-Mediated Annulations of Enamines
Xia, Biao,Chen, Wenjun,Zhao, Qiongli,Yu, Wenquan,Chang, Junbiao
supporting information, p. 2583 - 2587 (2019/04/17)
A novel annulation reaction of two enamine molecules with iodine under basic conditions to form 4-functionalized imidazolium salts has been established. In this reaction, iodine acts as both an iodinating reagent and a Lewis acid catalyst. Features of this synthetic method include facilitative preparation of substrates, no use of transition metals, mild reaction conditions, simplicity of operation, and gram scale synthesis.
PhIO/Et3N ? 3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines
Zhang, Yong,Zhao, Xiaoyuan,Zhuang, Chen,Wang, Senlin,Zhang-Negrerie, Daisy,Du, Yunfei
supporting information, p. 2107 - 2112 (2018/04/19)
A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2H-azirines through reactions with PhIF2 generated in situ by PhIO and Et3N ? 3HF in 1,2-dichroloethane, which features the hypervalent iodine reagents-mediated introduction of fluorine atom and formation of the 2H-azirine skeleton under metal-free conditions. The domino reaction is postulated to proceed via a PhIF2-mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. (Figure presented.).
Copper-promoted Chan-Lam coupling between enaminones and aryl boronic acids
Duan, Xiyan,Liu, Ning,Liu, Kun,Song, Yakun,Wang, Jia,Mao, Xianhua,Xu, Weidong,Yang, Shijie,Li, Huixian,Ma, Junying
supporting information, p. 4187 - 4190 (2018/10/24)
A novel copper-promoted N-arylation of enaminones with aromatic boronic acids has been developed, which provides an efficient way to synthesize N-aryl enaminones with a broad substrate scope and excellent functional group compatibility. The N-aryl enaminones could be converted into a series of highly valuable building blocks and bioactive compounds. Notably, in comparison with traditional methods, this alternative approach provides accesses to N-aryl enaminones bearing multiple aromatic rings.
Synthesis of β-enamino acid and heteroaryl acetic acid derivatives by Pd-catalyzed carbonylation of α-chloroimines and 2-chloromethyl aza-heterocycles
Perrone, Serena,Capua, Martina,Cannazza, Giuseppe,Salomone, Antonio,Troisi, Luigino
supporting information, p. 1421 - 1424 (2016/03/12)
β-Enamino esters or amides can be synthesized in a single step by a carbonylative coupling of α-chloroimines with alcohols or amines under Pd-catalysis. The methodology has been also applied to the preparation of heteroaryl acetic acid derivatives starting from chloromethyl heteroaromatic rings containing a C-N double bond. The in situ generation of a β-imino acylpalladium species has been proposed as a key step for the process.
HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
, p. 40950 - 40952 (2015/05/20)
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Synthesis of diversely substituted indoloquinolinones via Pd(II)/Cu(II)-mediated oxidative C-C bond formation and I(III)-mediated C-N bond formation
Zhang, Xiang,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
, p. 12750 - 12759 (2014/01/17)
A series of indoloquinolinones bearing different aromatic substitutents were readily synthesized starting from an aryl amine, a methyl 3-oxo-3-phenylpropanoate derivative, and methoxylamine through a series of reactions of coupling/enamination, oxidative
Cross-dehydrogenative coupling between enamino esters and ketones: Synthesis of tetrasubstituted pyrroles
Zhao, Miao,Wang, Fen,Li, Xingwei
, p. 1412 - 1415 (2012/05/04)
Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.
Highly regioselective AgNTf2-catalyzed intermolecular hydroamination of alkynes with anilines
Zhang, Xu,Yang, Bin,Li, Guangzhao,Shu, Xin,Mungra, Divyesh C.,Zhu, Jin
supporting information; experimental part, p. 622 - 626 (2012/04/04)
A facile and economic method for the fully regioselective and high-yielding protocol for the hydroamination of unsymmetrical internal alkynes under mild reaction conditions with AgNTf2 was developed. The materials are easily available from comm
