Sonogashira coupling with aqueous ammonia

被引:53
作者
Mori, A [1 ]
Ahmed, MSM [1 ]
Sekiguchi, A [1 ]
Masui, K [1 ]
Koike, T [1 ]
机构
[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan
关键词
D O I
10.1246/cl.2002.756
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The coupling reaction of terminal alkynes with organic halides, Sonogashira-(Hagihara) coupling, takes place with only 2 equivalents of dilute aqueous ammonia as ail additive. The reaction of phenylacetylene and 4-iodoanisole in the presence of 1 mol% of PdCl2(PPh3)(2), 2 mol% of CuI, and 2 equiv of aqueous ammonia in THF proceeds at room temperature for 6 h to afford the coupling product in a quantitative yield.
引用
收藏
页码:756 / 757
页数:2
相关论文
共 22 条
[1]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].
ALAMI, M ;
FERRI, F ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406
[2]   NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].
AMATORE, C ;
BLART, E ;
GENET, JP ;
JUTAND, A ;
LEMAIREAUDOIRE, S ;
SAVIGNAC, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839
[3]  
BOLM VPW, 2000, EUR J ORG CHEM, P3679
[4]   Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water [J].
Bumagin, NA ;
Sukhomlinova, LI ;
Luzikova, EV ;
Tolstaya, TP ;
Beletskaya, IP .
TETRAHEDRON LETTERS, 1996, 37 (06) :897-900
[5]  
CAMPBELL IB, 1994, ORGANOCOPPER REAGENT
[6]   PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA [J].
CASALNUOVO, AL ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4324-4330
[7]   Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].
Hundertmark, T ;
Littke, AF ;
Buchwald, SL ;
Fu, GC .
ORGANIC LETTERS, 2000, 2 (12) :1729-1731
[8]   Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina [J].
Kabalka, GW ;
Wang, L ;
Namboodiri, V ;
Pagni, RM .
TETRAHEDRON LETTERS, 2000, 41 (27) :5151-5154
[9]   Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: synthesis of aryl-substituted alkynylamides [J].
Koseki, Y ;
Omino, K ;
Anzai, S ;
Nagasaka, T .
TETRAHEDRON LETTERS, 2000, 41 (14) :2377-2380
[10]  
Mori A, 2001, SYNLETT, P649