31413-78-2

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 100-61-8 N-methylaniline 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 

Relevant academic research and scientific papers

Cu(acac)2 catalyzed oxidative C-H bond amination of azoles with amines under base-free conditions

This work reports a simple and efficient methodology for oxidative C-H bond amination of azoles with aromatic/aliphatic amines using copper-bis- acetylacetonate complex catalyst. The catalyst works very well in the absence of external acid or base and requires only molecular oxygen as an oxidant. The methodology is applicable for the oxidative C-H bond amination of various azoles with different types of aromatic/aliphatic amines for the synthesis of various aminoheterocycles with good to excellent yields.

Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C-N Coupling Protocol

Herein, a metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, which afforded numerous heteroaryl amines or their hydrochlorides without any external base. Further investigations elucidated that the basicity of amines and specific interactions derived from the X-ray crystallography analysis of 3j′·HCl played pivotal roles in the reactions. Moreover, this protocol was scalable to gram scales and applicable to drug molecules, which demonstrated its practical value for further applications.

Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes

CH, NH coupling of azole and thiophene derivatives takes place in the presence of a catalytic amount of Cu(OAc)2 and an additive. The reaction of azoles smoothly occurs with several amines and amides catalyzed by 20 mol % of Cu(OAc)2-2PPh3 and 4 equiv of NaOAc under O2 or in the presence of Ag2CO3 under N 2. The coupling reaction leads to a facile synthesis of a N-substituted analogue of 2,5-diarylthiazole, which shows photoluminescent properties with extended π-conjugation. Spectroscopic characteristics of the obtained thiazole derivatives are discussed by measurements of UV-vis absorption and photoluminescent spectra. Under the reaction conditions using Ag 2CO3 as an additive and Cu(OAc)2-2PPh 3 as a catalyst, thiophene derivatives also react with 2-pyrrolidone to undergo CH, NH amidation.

Direct amination of azoles via catalytic C-H, N-H Coupling

C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(0Ac)2

Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides

Detailed studies have been conducted to determine the activity of palladium catalysts for the amination of five-membered heterocyclic halides and to determine the factors that control the scope of this reaction. Palladium-catalyzed aminations of the electron-rich furanyl, thiophenyl, and indolyl halides and of the related 2-halogenated thiazoles, benzimidazole, and benzoxazole have been shown to occur with a subset of amines. Various combinations of palladium precursors and PtBu3 were tested as catalysts for reaction of 3-bromothiophene with N-methylaniline, and the fastest reactions occurred with the Pd(I) dimer, [PdBr(PtBu3)]2. The fastest aminations of thiazoles, benzimidazoles, and benzoxazoles occurred with the combination of palladium trifluoroacetate and PtBu3 as catalyst.