A binuclear Cu(I) complex as a novel catalyst towards the direct synthesis of N-2-aryl-substituted-1,2,3-triazoles from chalcones

被引:12
作者
Singh, Divya Pratap [1 ]
Allam, Bharat Kumar [1 ]
Singh, Rahul [1 ]
Singh, Krishna Nand [1 ]
Singh, Vinod Prasad [1 ]
机构
[1] Banaras Hindu Univ, Dept Chem, Inst Sci, Varanasi 221005, Uttar Pradesh, India
关键词
AZIDE-ALKYNE CYCLOADDITION; ONO DONOR LIGANDS; CLICK CHEMISTRY; REGIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT SYNTHESIS; CRYSTAL-STRUCTURE; TERMINAL ALKYNES; ZN(II) COMPLEXES; TRIAZOLE;
D O I
10.1039/c5ra27907k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A binuclear Cu(I) complex containing a N',N'-bis{(1H-indol-3-yl)methylene}oxalohydrazide (H(2)bioh) ligand has been synthesized and characterized. The molecular structures of the synthesized compounds have been determined by single crystal X-ray diffraction. The crystal structures are stabilized by inter- and intra-molecular pi-pi stacking and C-H center dot center dot center dot pi interactions. The Cu(I)-complex has successfully been employed as an efficient catalyst for one-pot operation involving the azide-chalcone click reaction and subsequent arylation has been developed. The complex exhibits excellent catalytic activity with significantly low catalyst loading. The overall process is insensitive to air and moisture and can be manipulated under ambient temperature with operational ease.
引用
收藏
页码:15518 / 15524
页数:7
相关论文
共 56 条
[1]  
Ali MA, 2001, INORG CHIM ACTA, V320, P1
[2]   An Efficient Phosphine-Free Heck Reaction in Water Using Pd(L-Proline)2 as the Catalyst Under Microwave Irradiation [J].
Allam, Bharat Kumar ;
Singh, Krishna Nand .
SYNTHESIS-STUTTGART, 2011, (07) :1125-1131
[3]   Click Dendrimers and Triazole-Related Aspects: Catalysts, Mechanism, Synthesis, and Functions. A Bridge between Dendritic Architectures and Nanomaterials [J].
Astruc, Didier ;
Liang, Liyuan ;
Rapakousiou, Amalia ;
Ruiz, Jaime .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (04) :630-640
[4]   Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].
Aucagne, Vincent ;
Leigh, David A. .
ORGANIC LETTERS, 2006, 8 (20) :4505-4507
[5]   "Clicking" Polymers or Just Efficient Linking: What Is the Difference? [J].
Barner-Kowollik, Christopher ;
Du Prez, Filip E. ;
Espeel, Pieter ;
Hawker, Craig J. ;
Junkers, Tanja ;
Schlaad, Helmut ;
Van Camp, Wim .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) :60-62
[6]   A highly active and reusable copper(I)-tren catalyst for the "click'' 1,3-dipolar cycloaddition of azides and alkynes [J].
Candelon, Nicolas ;
Lastecoueres, Dominique ;
Diallo, Abdou Khadri ;
Aranzaes, Jaime Ruiz ;
Astruc, Didier ;
Vincent, Jean-Marc .
CHEMICAL COMMUNICATIONS, 2008, (06) :741-743
[7]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[8]   Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles [J].
Chen, Yunfeng ;
Liu, Yuxiu ;
Petersen, Jeffrey L. ;
Shi, Xiaodong .
CHEMICAL COMMUNICATIONS, 2008, (28) :3254-3256
[9]   Synergistically Integrated Nanoparticles as Multimodal Probes for Nanobiotechnology [J].
Cheon, Jinwoo ;
Lee, Jae-Hyun .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (12) :1630-1640
[10]   Recyclable Catalytic Dendrimer Nanoreactor for Part-Per-Million CuI Catalysis of "Click" Chemistry in Water [J].
Deraedt, Christophe ;
Pinaud, Noel ;
Astruc, Didier .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) :12092-12098