Polystyrene resin supported palladium(0) (Pd@PR) nanocomposite mediated regioselective synthesis of 4-aryl-1-alkyl/(2-haloalkyl)-1H-1,2,3-triazoles and their N-vinyl triazole derivatives from terminal alkynes

被引:14
|
作者
Shil, Arun K. [1 ,2 ]
Kumar, Sandeep [1 ,2 ]
Sharma, Saurabh [1 ,2 ]
Chaudhary, Abha [1 ]
Das, Pralay [1 ,2 ]
机构
[1] CSIR, Nat Product Chem & Proc Dev, Inst Himalayan Bioresource Technol, Palampur 176061, Himachal Prades, India
[2] Acad Sci & Innovat Res, New Delhi, India
关键词
RECYCLABLE HETEROGENEOUS CATALYST; CLICK CHEMISTRY; AZIDE; NANO/MICROPARTICLE; POLYMER; STYRYL;
D O I
10.1039/c4ra15133j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient general methodology has been developed for sequential one-pot synthesis of 4-aryl-1-alkyl-1H-1,2,3-triazoles influenced by polystyrene resin supported palladium(0) (Pd@PR) nanocomposite as a heterogeneous catalyst. The present work particularly emphasizes the synthesis of 4-aryl-1-(2-haloalkyl)-1H-1,2,3-triazoles through the selective mono-azidation of 1,2-dihaloethane and subsequent Pd@PR mediated 1,3-dipolar cycloaddition with terminal aryl alkynes. Potassium carbonate promoted dehydrohalogenation of synthesized 4-aryl-1-(2-haloalkyl)-1H-1,2,3-triazoles gave the corresponding N-vinyl derivatives (often used as building blocks for polymers) which are further utilized in the synthesis of 4-aryl-1-(2-arylalkenyl)-1H1,2,3-triazoles following a Pd@PR catalyzed Heck coupling approach. Furthermore, microwave assisted one pot dehydrochlorination and Heck strategy was adopted to afford 4-phenyl-1-styryl-1H-1,2,3-triazole under Pd@PR catalyzed conditions using iodobenzene as a phenylating agent.
引用
收藏
页码:11506 / 11514
页数:9
相关论文
共 1 条