Synthesis of Ynones via Recyclable Polystyrene-Supported Palladium(0) Complex Catalyzed Acylation of Terminal Alkynes with Acyl Chlorides under Copper- and Solvent-Free Conditions

被引:22
作者
Bakherad, Mohammad [1 ]
Keivanloo, Ali [1 ]
Bahramian, Bahram [1 ]
Jajarmi, Saeideh [1 ]
机构
[1] Shahrood Univ Technol, Sch Chem, Shahrood, Iran
关键词
copper-free; solvent-free; supported catalyst; Sonogashira coupling; acyl chloride; ynone; POT 3-COMPONENT SYNTHESIS; ACID-CHLORIDES; FERROCENYLETHYNYL KETONES; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; ACETYLENIC KETONES; CYCLOISOMERIZATION;
D O I
10.1055/s-0030-1259322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a highly efficient method for the copper- and solvent-free coupling reaction of acyl chlorides and terminal alkynes catalyzed by 1-phenyl-1,2-propanedione-2-oxime thiosemicarbazone-functionalized polystyrene resin-supported Pd(0) complex is described. Acyl chlorides are easily coupled with terminal alkynes, giving good to high yields in the presence of a low catalyst loading (1 mol% Pd) in Et3N at room temperature under aerobic conditions. After centrifugation, the supported catalyst can be recycled and reused several times with only a slight decrease in activity.
引用
收藏
页码:311 / 314
页数:4
相关论文
共 29 条
[21]   A NOVEL PALLADIUM-CATALYZED REARRANGEMENT OF ACETYLENIC KETONES TO FURANS [J].
SHENG, HY ;
LIN, SY ;
HUANG, YZ .
TETRAHEDRON LETTERS, 1986, 27 (40) :4893-4894
[22]  
TOHDA Y, 1977, SYNTHESIS-STUTTGART, P777
[23]   Synthetic stitching with silicon: Geminal alkylation-hydroxylation of alkynyl carbonyl compounds [J].
Trost, BM ;
Ball, ZT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :13942-13944
[24]   A SIMPLE SYNTHESIS OF DIENONES VIA ISOMERIZATION OF ALKYNONES EFFECTED BY PALLADIUM CATALYSTS [J].
TROST, BM ;
SCHMIDT, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2301-2303
[25]  
Vereshchagin L. I., 1966, ORG KHIM, V2, P1895
[26]   Stereoselective total synthesis of (-)-borrelidin [J].
Vong, BG ;
Kim, SH ;
Abraham, S ;
Theodorakis, EA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3947-3951
[27]   FRIEDEL-CRAFTS REACTIONS OF BIS(TRIMETHYLSILYL)POLYYNES WITH ACYL CHLORIDES - USEFUL ROUTE TO TERMINAL-ALKYNYL KETONES [J].
WALTON, DRM ;
WAUGH, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 37 (01) :45-&
[28]   A facile synthesis of conjugated acetyl ketones by Pd(II)-Cu(I) doped KF/Al2O3-catalyzed under microwave irradiation [J].
Wang, JX ;
Wei, BG ;
Huang, DF ;
Hu, YL ;
Bai, L .
SYNTHETIC COMMUNICATIONS, 2001, 31 (21) :3337-3343
[29]   Synthesis of ferrocenylethynyl ketones by coupling of ferrocenylethyne with acyl chlorides [J].
Yin, JX ;
Wang, XJ ;
Liang, YM ;
Wu, XL ;
Chen, BH ;
Ma, YX .
SYNTHESIS-STUTTGART, 2004, (03) :331-333