Zn(OAc)2•2H2O:: a versatile catalyst for the one-pot synthesis of propargylamines

被引：143
作者：
Ramu, Enugala
Varala, Ravi
Sreelatha, Nuvula
Adapa, Srinivas R. [1 ]
机构：
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
[2] Univ Nova Lisboa, Dept Quim, Lab 202, FCT, P-2829516 Caparica, Portugal
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 40期
关键词：
three-component coupling; zinc acetate; propargylamines; catalysis;
D O I：
10.1016/j.tetlet.2007.07.196
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An inexpensive and readily available catalyst, Zn(OAc)(2)center dot 2H(2)O is successfully evaluated for effective one-pot synthesis of propargylamines with moderate to excellent yields for most of the substrates screened, without the need of base, co-catalyst or additive in the presence of air. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7184 / 7190
页数：7
相关论文
共 39 条
[1]   Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].
Akullian, LC ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247
[2]  
[Anonymous], ORGANOMAGNESIUM METH
[3]  
[Anonymous], ORGANOLITHIUM METHOD
[4]   Metal catalyzed multicomponent syntheses of secondary propargylamides and oxazoles from silylimines, acid chlorides, and alkynes [J].
Black, DA ;
Arndtsen, BA .
TETRAHEDRON, 2005, 61 (48) :11317-11321
[5]   Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes [J].
Colombo, F ;
Benaglia, M ;
Orlandi, S ;
Usuelli, F ;
Celentano, G .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2064-2070
[6]   Highly diastereoselective synthesis of N-tert-butylsulfinylpropargylamines through direct addition of Alkynes to N-tert-butanesulfinimines [J].
Ding, Chang-Hua ;
Chen, Dong-Dong ;
Luo, Zhi-Bin ;
Dai, Li-Xin ;
Hou, Xue-Long .
SYNLETT, 2006, (08) :1272-1274
[7]   Zn-alkynylide additions to acyl iminiums [J].
Fischer, C ;
Carreira, EM .
ORGANIC LETTERS, 2004, 6 (09) :1497-1499
[8]   Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex [J].
Fischer, C ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (26) :4319-4321
[9]   Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246
[10]   Highly enantioselective synthesis of propargylamines using (mesitylmethyl)benzylamine [J].
Gommermann, N ;
Knochel, P .
SYNLETT, 2005, (18) :2799-2801
1234