Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst

被引:119
作者
Hajipour, Abdol R. [1 ,2 ]
Rezaei, Fatemeh [1 ]
Khorsandi, Zahra [1 ]
机构
[1] Isfahan Univ Technol, Dept Chem, Esfahan 84156, Iran
[2] Univ Wisconsin, Sch Med, Dept Neurosci, Madison, WI 53706 USA
关键词
EFFICIENT HETEROGENEOUS CATALYST; PALLADIUM NANOPARTICLES; CARBON NANOTUBES; SUZUKI-MIYAURA; RECOVERABLE CATALYST; RECYCLABLE CATALYST; HIGHLY EFFICIENT; BOND FORMATION; MEDIATED HECK; IONIC LIQUIDS;
D O I
10.1039/c6gc03377f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chitosan ( CS) is a porous, self-standing, nanofibrillar microsphere that can be used as a metal carrier. Amino groups on CS enable to modulate cobalt coordination using a safe organic ligand ( methyl salicylate). This catalyst efficiently promotes Heck cross-coupling of a large library of functional substrates under mild and sustainable conditions ( polyethylene glycol as solvent at 80 degrees C in a short time (1h)). The cobalt complex was also used as a heterogeneous, efficient, inexpensive, and green catalyst for Sonogashira cross-coupling reactions. The reactions of various aryl halides and phenylacetylene provided the corresponding products in moderate to good yields. More importantly, this phosphine, copper, and palladium-free catalyst was stable under the reaction conditions and could be easily reused using an external magnet for at least five successive runs without a discernible decrease in its catalytic activity.
引用
收藏
页码:1353 / 1361
页数:9
相关论文
共 68 条
[1]  
[Anonymous], ADV SYNTH CATAL
[2]   Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].
Arpad Molnar .
CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320
[3]   Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].
Astruc, Didier .
INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894
[4]   Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine [J].
Astruc, Didier ;
Boisselier, Elodie ;
Ornelas, Catia .
CHEMICAL REVIEWS, 2010, 110 (04) :1857-1959
[5]   Copper(II) oxide on aluminosilicate mediated Heck coupling of styrene with aryl halides in water [J].
Babu, S. Ganesh ;
Neelakandeswari, N. ;
Dharmaraj, N. ;
Jackson, S. David ;
Karvembu, R. .
RSC ADVANCES, 2013, 3 (21) :7774-7781
[6]   Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].
Barluenga, Jose ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   Cobalt-Catalyzed Cross-Coupling Reactions [J].
Cahiez, Gerard ;
Moyeux, Alban .
CHEMICAL REVIEWS, 2010, 110 (03) :1435-1462
[9]   Heck reaction catalyzed by nanosized palladium on chitosan in ionic liquids [J].
Calò, V ;
Nacci, A ;
Monopoli, A ;
Fornaro, A ;
Sabbatini, L ;
Cioffi, N ;
Ditaranto, N .
ORGANOMETALLICS, 2004, 23 (22) :5154-5158
[10]   Heterogeneous palladium catalysts for a new one-pot chemical route in the synthesis of fragrances based on the Heck reaction [J].
Climent, Maria Jose ;
Corma, Avelino ;
Iborra, Sara ;
Mifsud, Maria .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1949-1954