A novel and convenient copper-catalyzed three-component coupling of aldehydes, alkynes, and hydroxylamines leading to propargylamines

被引:11
作者
Guo, Na [1 ,2 ]
Ji, Jian-Xin [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper catalysis; Three-component; Aldehyde; Alkyne; Hydroxylamine; Propargylamine; C-H ACTIVATION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ONE-POT SYNTHESIS; SECONDARY-AMINES; EFFICIENT; SILVER; COMPLEX; WATER; GOLD; CYCLIZATION;
D O I
10.1016/j.tetlet.2012.03.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first copper-catalyzed direct three-component coupling reaction of aldehydes, alkynes, and hydroxylamines for the synthesis of propargylamines has been developed under mild conditions, which has the advantages of ready availability of catalyst as well as operation simplicity. The present protocol provides an appealing alternative for the construction of propargylamines in a simple and one-pot procedure. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4797 / 4801
页数:5
相关论文
共 51 条
[1]   SUICIDE ENZYME INACTIVATORS [J].
ABELES, RH ;
MAYCOCK, AL .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (09) :313-319
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[4]  
2-A
[5]   Enantioselective one-pot three-component synthesis of propargylamines [J].
Bisai, Alakesh ;
Singh, Vinod K. .
ORGANIC LETTERS, 2006, 8 (11) :2405-2408
[6]   Gold-Catalyzed Direct Intermolecular Coupling of Ketones, Secondary Amines, and Alkynes: A Facile and Versatile Access to Propargylic Amines Containing a Quaternary Carbon Center [J].
Cheng, Ming ;
Zhang, Qiang ;
Hu, Xiao-Yu ;
Li, Bo-Gang ;
Ji, Jian-Xin ;
Chan, Albert S. C. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1274-1278
[7]   Hydroxyapatite supported copper catalyst for effective three-component coupling [J].
Choudary, BM ;
Sridhar, C ;
Kantam, ML ;
Sreedhar, B .
TETRAHEDRON LETTERS, 2004, 45 (39) :7319-7321
[8]   CHAIN-EXTENSION OF CARBOHYDRATES .4. A STEREOCONTROLLED SYNTHESIS OF A LINCOSAMINE PRECURSOR [J].
CZERNECKI, S ;
VALERY, JM .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :767-770
[9]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[10]  
2-U