Copper(I) Zeolites as Heterogeneous and Ligand-Free Catalysts: [3+2] Cycloaddition of Azomethine Imines

被引：107

作者：

Keller, Murielle ^{[2
]}

Sido, Abdelkarim Sani Souna ^{[1
,2
]}

Pale, Patrick ^{[1
]}

Sommer, Jean ^{[2
]}

机构：

[1] Inst Chim Strasbourg, Lab Synthese & React Organ, F-67000 Strasbourg, France

[2] Inst Chim Strasbourg, Lab Physicochim Hydrocarbures, F-67000 Strasbourg, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 12期

关键词：

click chemistry; copper; cycloaddition; heterogeneous catalysis; zeolites; CU-I-ZEOLITES; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; TERMINAL ALKYNES; YLIDES; AGENTS; ACIDS;

D O I：

10.1002/chem.200802191

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper(I)-exchanged zeolites were used as heterogeneous ligand-free catalysts for [3+2] cycloaddition of azomethine ylides, which allows versatile, efficient, and highly regioselective synthesis of pyrazolone derivatives. These cheap and easy-to-prepare catalysts exhibit wide scope and compatibility with functional groups. They are very simple to use, easy to remove (by simple filtration), and recyclable (up to six times without loss of activity)

引用

页码：2810 / 2817

页数：8

共 50 条

[1] Click Chemistry in zeolites: Copper(I) zeolites as new heterogeneous and ligand-free catalysts for the Huisgen [3+2] cycloaddition
Chassaing, Stefan
Sido, Abdelkarim Sani Souna
Alix, Aurelien
Kumarraja, Mayilvasagam
Pale, Patrick
Sommer, Jean
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) : 6713 - 6721
[2] Thermal [3+2] Cycloaddition of Aromatic Azomethine Imines with Allenoates
Zhang, Lei
Jing, Chengfeng
Liu, Honglei
Wang, Bo
Li, Zhen
Jiang, Hui
Yu, Hao
Guo, Hongchao
SYNTHESIS-STUTTGART, 2013, 45 (01): : 53 - 64
[3] Catalytic asymmetric [3+2] cycloaddition of azomethine imines with ketenes
Mondal, Mukulesh
Kerrigan, Nessan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[4] [3+2] CYCLOADDITION OF SELENO- AND THIOALDEHYDES WITH CYCLIC AZOMETHINE IMINES
Maeda, Hajime
Takamizawa, Yusuke
Segi, Masahito
HETEROCYCLES, 2012, 84 (01) : 393 - 400
[5] Alkaloid-Catalyzed Enantioselective [3+2] Cycloaddition of Ketenes and Azomethine Imines
Mondal, Mukulesh
Wheeler, Kraig A.
Kerrigan, Nessan J.
ORGANIC LETTERS, 2016, 18 (16) : 4108 - 4111
[6] Gold catalyzed [3+2] cycloaddition of N-allenyl amides with azomethine imines
Zhou, Wen
Li, Xiao-Xiao
Li, Guo-Hua
Wu, Yun
Chen, Zili
CHEMICAL COMMUNICATIONS, 2013, 49 (34) : 3552 - 3554
[7] Facile Synthesis of 1,2,4-trisubstituted Imidazoles via Aerobic Copper Catalyzed Ligand-free [3+2] Cycloaddition
Li, Wei
Tian, Weixiang Jiao Wan
Lei, Ming
LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (05) : 386 - 392
[8] [3+2]-Cycloadditions of Azomethine Imines and Ynolates
Winterton, Sarah E.
Ready, Joseph M.
ORGANIC LETTERS, 2016, 18 (11) : 2608 - 2611
[9] Base- and ligand-free copper catalysis for the alkynylation of imines
Larsen, Catharine H.
Meyet, Courtney E.
Pierce, Conor J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[10] Enantioselective Copper-Catalyzed [3+3] Cycloaddition of Azomethine Ylides with Azomethine Imines
Guo, Hongchao
Liu, Honglei
Zhu, Fu-Lin
Na, Risong
Jiang, Hui
Wu, Yang
Zhang, Lei
Li, Zhen
Yu, Hao
Wang, Bo
Xiao, Yumei
Hu, Xiang-Ping
Wang, Min
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) : 12641 - 12645

← 1 2 3 4 5 →