21326-90-9Relevant academic research and scientific papers
Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of Benzothiazoles to 1-Amino-N-(2-(phenylthio)phenyl)methanimine
Zheng, Nian,Liu, Ce,Ding, Ya-Nan,Shi, Wei-Yu,Zhang, Bo-Sheng,Liang, Yong-Min
, p. 7666 - 7673 (2020)
Copper-catalyzed three-component redox-neutral ring opening of benzothiazoles with aryl iodides and O-benzoyl hydroxylamines for the synthesis of 1-amino-N-(2-(phenylthio)phenyl)methanimine has been developed. This one-pot reaction undergoes C-S and N-O bond cleavage and new C-S and C-N bond construction. Several control experiments excluded a free radical procedure and also demonstrated the secondary amine as a possible intermediate, which was vital to the catalytic reaction. Meanwhile, the deuteration experiment got rid of the C-H activation dehydroisomerization of the benzothiazole mechanism.
Copper-catalyzed aerobic oxidation for the amination of benzoxazole under air
Cao, Ke,Wang, Jia-Ling,Wang, Lin-Hui,Li, Yuan-Yuan,Yu, Xing-Hua,Huang, Yawen,Yang, Junxiao,Chang, Guanjun
, p. 2848 - 2853 (2014/09/17)
A practical copper-catalyzed aerobic oxidation for the amination of benzoxazole with secondary amine has been discovered. This reaction has proved to be effective to a variety of amines with lower catalyst loading amount, and only oxygen in air is required to facilitate this transformation. A copper-catalyzed/amine-induced ring opening of the benzoxazole and recyclization mechanism was also proposed.
Cooperative catalysis with aldehydes and copper: Development and application in aerobic oxidative C-H amination at room temperature
Xie, Yinjun,Qian, Bo,Xie, Pan,Huang, Hanmin
supporting information, p. 1315 - 1322 (2013/06/27)
A conceptually new cooperative catalytic system via a synergistic combination of aldehyde and copper catalysis has been established based on systemic mechanistic studies. This new cooperative catalysis has been successfully applied in the direct aerobic oxidative C-H amination of azoles at room temperature, which was previously realized under harsh conditions. Mechanistic studies including isotopic labeling experiments and kinetic isotope effect (KIE) experiments support a reaction pathway that involves formation of an aminal, hydrolysis of the aminal to generate the copper-amide species, subsequent C-H amination and re-oxidation of copper(I) to copper(II) by oxygen. It not only provides an efficient method to realize the oxidative C-H amination of benzoxazoles with free amines at room temperature, but also paves the way for establishing new C-N bond formation reactions by using this efficient cooperative catalysis. Copyright
Copper-catalyzed oxidative amination of benzoxazoles via C-H and C-N bond activation: A new strategy for using tertiary amines as nitrogen group sources
Guo, Shengmei,Qian, Bo,Xie, Yinjun,Xia, Chungu,Huang, Hanmin
supporting information; experimental part, p. 522 - 525 (2011/04/18)
An efficient and conceptually new method for oxidative amination of azoles with tertiary amines via copper-catalyzed C-H and C-N bond activation has been developed. This protocol can be performed in the absence of external base and only requires atmospheric oxygen as oxidant. The catalyst system is very simple and efficient, which opens a new way for using tertiary amines as nitrogen group sources for C-N bond formation reactions.
