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
[1]   Synthesis of ynones by palladium-catalyzed acylation of terminal alkynes with acid chlorides [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (05) :1615-1619
[2]   A copper- and solvent-free coupling of acid chlorides with terminal alkynes catalyzed by a polystyrene-supported palladium(0) complex under aerobic conditions [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Rajaie, Mahbobeh .
TETRAHEDRON LETTERS, 2010, 51 (01) :33-35
[3]   catena-Poly[zinc(II)-μ-aqua-κ2O:O-bis(μ-quinoline-4-carboxylato-κ2O:O′)] [J].
Chen, Jin-Xi ;
Meng, Wei-Wei .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :M873-U474
[4]   A remarkably efficient coupling of acid chlorides with alkynes in water [J].
Chen, L ;
Li, CJ .
ORGANIC LETTERS, 2004, 6 (18) :3151-3153
[5]   Studies on copper(I) catalysed cross-coupling reactions:: A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones [J].
Chowdhury, C ;
Kundu, NG .
TETRAHEDRON, 1999, 55 (22) :7011-7016
[6]   Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes [J].
Cox, RJ ;
Ritson, DJ ;
Dane, TA ;
Berge, J ;
Charmant, JPH ;
Kantacha, A .
CHEMICAL COMMUNICATIONS, 2005, (08) :1037-1039
[7]   THE PREPARATION OF ACETYLENIC KETONES USING SOLUBLE SILVER ACETYLIDES [J].
DAVIS, RB ;
SCHEIBER, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (08) :1675-1678
[8]   Stereoselective synthesis of stannyl enones via palladium-catalyzed and free radical hydrostannation of alkynyl ketones with trineophyltin hydride [J].
Dodero, VI ;
Koll, LC ;
Faraoni, MB ;
Mitchell, TN ;
Podestá, JC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10087-10091
[9]   Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones [J].
Kel'in, AV ;
Gevorgyan, V .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :95-98
[10]   A novel Cu-assisted cycloisomerization of alkynyl imines: Efficient synthesis of pyrroles and pyrrole-containing heterocycles [J].
Kel'in, AV ;
Sromek, AW ;
Gevorgyan, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2074-2075