Microwave-accelerated Mizoroki-Heck and Sonogashira cross-coupling reactions in water using a heterogeneous palladium(II)-precatalyst

被引:52
作者
Dawood, Kamal M.
Solodenko, Wladimir
Kirschning, Andreas [1 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, Schneiderberg 1B, D-30167 Hannover, Germany
[2] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
关键词
catalysis; immobilization; microwave; Mizoroki-Heck reaction; palladium; Sonogashira reaction;
D O I
10.3998/ark.5550190.0008.510
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic activity of a 2-pyridinealdoxime-based Pd(II)-complex covalently anchored via the oxime moiety to a glass/polymer composite material was evaluated both under thermal as well as microwave (mu w) irradiating conditions in water in Mizoroki-Heck as well as Sonogashira C-C cross-coupling reactions. Synthesis of benzo[b] furan derivatives via Sonogashira cross coupling reaction was achieved when ortho-halo-phenols were employed as aryl halides. The stability and reusability of this Pd-precatalyst was part of the present study.
引用
收藏
页码:104 / 124
页数:21
相关论文
共 126 条
[21]   SYNTHESIS OF SUBSTITUTED CINNAMIC-ACIDS AND CINNAMONITRILES VIA PALLADIUM CATALYZED COUPLING REACTIONS OF ARYL HALIDES WITH ACRYLIC-ACID AND ACRYLONITRILE IN AQUEOUS-MEDIA [J].
BUMAGIN, NA ;
MORE, PG ;
BELETSKAYA, IP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 371 (03) :397-401
[22]   DEVELOPMENT AND APPLICATION OF A CONTINUOUS MICROWAVE REACTOR FOR ORGANIC-SYNTHESIS [J].
CABLEWSKI, T ;
FAUX, AF ;
STRAUSS, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3408-3412
[23]   NATURALLY-OCCURRING DIBENZOFURANS .4. SYNTHESIS OF DIBENZOFURANDIOLS BY ANNELATION OF BENZOFURANS [J].
CARVALHO, CF ;
SARGENT, MV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (07) :1605-1612
[24]   Polymer-supported catalysis in synthetic organic chemistry [J].
Clapham, B ;
Reger, TS ;
Janda, KD .
TETRAHEDRON, 2001, 57 (22) :4637-4662
[25]  
Crisp GT, 1998, CHEM SOC REV, V27, P427
[26]   Chemistry of aminophenols.: Part 3:: First synthesis of nitrobenzo[b]furans via a coupling-cyclization approach [J].
Dai, WM ;
Lai, KW .
TETRAHEDRON LETTERS, 2002, 43 (51) :9377-9380
[27]   Combining enabling techniques in organic synthesis: solid-phase-assisted catalysis under microwave conditions using a stable Pd(II)-precatalyst [J].
Dawood, KM ;
Kirschning, A .
TETRAHEDRON, 2005, 61 (51) :12121-12130
[28]   Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].
de la Hoz, A ;
Díaz-Ortiz, A ;
Moreno, A .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178
[29]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[30]   Homeopathic ligand-free palladium as a catalyst in the Heck reaction. A comparison with a palladacycle [J].
de Vries, AHM ;
Mulders, JMCA ;
Mommers, JHM ;
Henderickx, HJW ;
de Vries, JG .
ORGANIC LETTERS, 2003, 5 (18) :3285-3288