21326-90-9Relevant articles and documents
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.
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
