19968-55-9Relevant academic research and scientific papers
Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions
Song, A-Xiang,Zeng, Xiao-Xiao,Ma, Bei-Bei,Xu, Chang,Liu, Feng-Shou
, p. 3524 - 3534 (2020/10/09)
With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.
Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions
Ma, Bei-Bei,Lan, Xiao-Bing,Shen, Dong-Sheng,Liu, Feng-Shou,Xu, Chang
, p. 13 - 22 (2019/06/27)
A highly efficient and practical protocol has been developed for the synthesis of 5-(hetero)arylated thiazole derivatives via an N-heterocyclic carbene palladium (Pd-NHC) complex catalyzed direct C-H arylation reaction. Utilization of this methodology, th
Camphyl-based α-diimine palladium complexes: Highly efficient precatalysts for direct arylation of thiazoles in open-air
Chen, Fu-Min,Lu, Dong-Dong,Hu, Li-Qun,Huang, Ju,Liu, Feng-Shou
, p. 5731 - 5736 (2017/07/22)
Based on the strategy of the development of phosphine-free palladium-catalyzed direct C-H arylation, a series of camphyl-based α-diimine palladium complexes bearing sterically bulky substituents were synthesized and characterized. The palladium complexes
A convenient phosphine-free palladium-catalyzed direct arylation of thiazole under mild aerobic conditions
He, Xiao-Xi,Li, Yan-Fang,Huang, Ju,Shen, Dong-Sheng,Liu, Feng-Shou
, p. 58 - 66 (2015/12/30)
A series of bulky amine palladium complexes {[(Ar-NH2)2PdCl2]} were synthesized and characterized. The catalytic activity of the palladium complexes was evaluated via the direct C-H arylation of thiazoles with aryl bromide
Decarboxylative cross-coupling of azoyl carboxylic acids with aryl halides
Zhang, Fengzhi,Greaney, Michael F.
supporting information; experimental part, p. 4745 - 4747 (2010/12/24)
Decarboxylative cross-coupling of thiazole and oxazole-5-carboxylic acids with aryl halides is reported. Under a bimetallic system of catalytic palladium and a stoichiometric silver carbonate, a variety of (hetero)arylated azoles can be prepared in excell
Direct arylation of thiazoles on water
Turner, Gemma L.,Morris, James A.,Greaney, Michael F.
, p. 7996 - 8000 (2008/09/17)
Wetter is better: The direct arylation of thiazoles on water is quicker, cleaner, and higher-yielding than arylation in organic solvents. The reaction works under mild conditions for an array of aryl iodides, producing 2,5-diaryl thiazoles in excellent yields. Importantly, novel bi-heteroaryl compounds are produced without the requirement for stoichiometric organometallic coupling agents. (Figure Presented).
