54175-73-4Relevant articles and documents
Cu(OAc)2-Mediated benzimidazole-directed C-H cyanation using 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source
Zhang, Tianyou,Qiao, Jingyi,Song, He,Xu, Feng,Liu, Xiaochong,Xu, Chunzhao,Ma, Junjie,Liu, Hao,Sun, Zhizhong,Chu, Wenyi
supporting information, p. 9084 - 9089 (2019/06/18)
A new protocol for the Cu(OAc)2-mediated cyanation of arenes using benzimidazole as the directing group with 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was developed. A series of cyano derivatives were facilely and conveniently obtained in moderate to good yields by using this method. The C-H activation catalytic system was originally applied to the C(sp2)-H cyanation of the aryl/heteroaryl to synthesize 2-(1H-benzo[d]imidazol-2-yl)aryl nitriles. There were 19 new compounds in the synthesized 20 cyanide products. In this reaction, 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was originally employed in the C(sp2)-H cyanation of the arenes. In addition, a fluorescent material 5a was obtained by derivative reactions of the obtained cyanide product 3.
Direct C-H bond arylation of (benzo)oxazoles with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex
Shen, Xiao-Bao,Zhang, Yun,Chen, Wen-Xin,Xiao, Zheng-Kang,Hu, Ting-Ting,Shao, Li-Xiong
supporting information, p. 1984 - 1987 (2014/05/06)
The direct C-H bond arylation of (benzo)oxazoles with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various aryl chlorides were successfully applied as the arylating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzo)oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.
Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium-diphosphine catalyst
Derridj, Fazia,Djebbar, Safia,Benali-Baitich, Ouassini,Doucet, Henri
, p. 135 - 144 (2008/03/30)
Through the use of PdCl(dppb)(C3H5) as a catalyst, a range of aryl bromides and chlorides undergoes coupling via C-H bond activation/functionalization reaction with oxazole or benzoxazole in good yields. This air-stable catalyst can be used at low loadings with several substrates. Surprisingly, better results in terms of substrate/catalyst ratio were obtained in several cases using electron-excessive aryl bromides than with the electron-deficient ones. This seems to be mainly due to the relatively low thermal stability of some of the 2-arylbenzoxazoles formed with electron-deficient aryl halides. With these substrates, in order to obtain higher yields of product, the reactions had to be performed at a lower temperature (100-120 °C) using a larger amount of catalyst. On the other hand, in the presence of the most stable products, the reactions were performed at 150 °C using as little as 0.2 mol% catalyst. Arylation of benzoxazole with heteroaryl bromides also gave the coupling products in moderate to high yields using 0.2-5 mol% catalyst. With this catalyst, electron-deficient aryl chloride such as 4-chlorobenzonitrile, 4-chloroacetophenone or 2-chloronitrobenzene have also been used successfully.
