Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: synthesis of aryl-substituted alkynylamides

被引:66
作者
Koseki, Y [1 ]
Omino, K [1 ]
Anzai, S [1 ]
Nagasaka, T [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan
关键词
alkynes; coupling reactions; silicon and compounds; palladium catalyst;
D O I
10.1016/S0040-4039(00)00167-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct cross-coupling reaction of 5-trimethylsilyl-4-pentynamides (alkynylsilanes) 1 with aryl iodides, promoted by silver carbonate in the presence of palladium catalyst, afforded aryl-substituted alkynylamides 2, which readily underwent cyclization to form benzylidenelactams 3. This coupling reaction proved to be a useful for synthesis of aryl-substituted alkynes. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2377 / 2380
页数:4
相关论文
共 23 条
[1]   A straightforward synthesis of symmetrical polyendiynes by dimerization reactions of silyl derivatives [J].
Babudri, F ;
Fiandanese, V ;
Marchese, G ;
Punzi, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 566 (1-2) :251-257
[2]   Synthesis of enynes and epoxyenynes by coupling: use of a new set of catalysts based on Pd-Ag salts [J].
Bertus, P ;
Pale, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 567 (1-2) :173-180
[3]   HIGHLY SELECTIVE CROSS-COUPLING REACTION OF ORGANOSILICON COMPOUNDS MEDIATED BY FLUORIDE-ION AND PD CATALYST [J].
HATANAKA, Y ;
HIYAMA, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1990, 48 (09) :834-843
[4]   A ONE-POT SYNTHESIS OF CONJUGATED DIENYNES BY PALLADIUM-MEDIATED 3 COMPONENT CROSS-COUPLING REACTION [J].
HATANAKA, Y ;
MATSUI, K ;
HIYAMA, T .
TETRAHEDRON LETTERS, 1989, 30 (18) :2403-2406
[5]  
Huang SL, 1999, TETRAHEDRON LETT, V40, P3347
[6]   Copper(I) salt promoted homo-coupling reaction of organosilanes [J].
Ikegashira, K ;
Nishihara, Y ;
Hirabayashi, K ;
Mori, A ;
Hiyama, T .
CHEMICAL COMMUNICATIONS, 1997, (11) :1039-1040
[7]   Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents [J].
Ito, H ;
Arimoto, K ;
Sensui, H ;
Hosomi, A .
TETRAHEDRON LETTERS, 1997, 38 (22) :3977-3980
[8]   TETRAPYRROLES .4. A HIGHLY EFFICIENT SYNTHESIS OF HOMOCHIRAL DIHYDROPYRROMETHENONES VIA PD(0) MEDIATED COUPLING OF IODOPYRROLES AND ACETYLENIC AMIDES [J].
JACOBI, PA ;
RAJESWARI, S .
TETRAHEDRON LETTERS, 1992, 33 (42) :6235-6238
[9]   Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides [J].
Jacobi, PA ;
Brielmann, HL ;
Hauck, SI .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5013-5023
[10]   Intramolecular cyclization of β-alkynylpropanamides to γ-alkylidene-γ-butyrolactams [J].
Koseki, Y ;
Kusano, S ;
Nagasaka, T .
TETRAHEDRON LETTERS, 1998, 39 (21) :3517-3520