An aluminum(iii) picket fence phthalocyanine-based heterogeneous catalyst for ring-expansion carbonylation of epoxides

被引:26
作者
Jiang, Jianwei [1 ]
Yoon, Sungho [1 ]
机构
[1] Kookmin Univ, Dept Appl Chem, 861-1 Jeongneung Dong, Seoul 02707, South Korea
关键词
BETA-LACTONES; INTRINSIC MICROPOROSITY; BUILDING-BLOCKS; COBALT; POLYMERS; POLYMERIZATION; BUTYROLACTONE; COMPLEXES; FRAMEWORK; MECHANISM;
D O I
10.1039/c8ta11877a
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An effective heterogeneous catalyst for ring-expansion carbonylation of epoxides may have additional advantages over the homogeneous counterpart in terms of facile product separation and recyclability. A new Al(iii) picket fence phthalocyanine complex was synthesized and directly knitted using the Friedel-Crafts reaction to prepare a solid porous network, which was ultimately used to immobilize [Co(CO)(4)](-) ions. The resulting heterogeneous catalyst, [Lewis acid](+)[Co(CO)(4)](-), efficiently catalyzes the conversion of various epoxides into the corresponding beta-lactones with high selectivity (99%) and stoichiometric conversion under mild reaction conditions, along with good functional group tolerance.
引用
收藏
页码:6120 / 6125
页数:6
相关论文
共 51 条
[21]   Practical β-lactone synthesis:: Epoxide carbonylation at 1 atm [J].
Kramer, John W. ;
Lobkovsky, Emil B. ;
Coates, Geoffrey W. .
ORGANIC LETTERS, 2006, 8 (17) :3709-3712
[22]   Meinwald-type rearrangement of monosubstituted epoxides to methyl ketones using an [Al porphyrin]+[Co(CO)4]- catalyst [J].
Lamb, Jessica R. ;
Jung, Yukyung ;
Coates, Geoffrey W. .
Organic Chemistry Frontiers, 2015, 2 (04) :346-349
[23]   Synthesis of β-lactones by the regioselective, cobalt and Lewis acid catalyzed carbonylation of simple and functionalized epoxides [J].
Lee, JT ;
Thomas, PJ ;
Alper, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5424-5426
[24]   Highly Dispersed Pd Catalyst Locked in Knitting Aryl Network Polymers for Suzuki-Miyaura Coupling Reactions of Aryl Chlorides in Aqueous Media [J].
Li, Buyi ;
Guan, Zhenhong ;
Wang, Wei ;
Yang, Xinjia ;
Hu, Jianglin ;
Tan, Bien ;
Li, Tao .
ADVANCED MATERIALS, 2012, 24 (25) :3390-3395
[25]   A New Strategy to Microporous Polymers: Knitting Rigid Aromatic Building Blocks by External Cross-Linker [J].
Li, Buyi ;
Gong, Ruini ;
Wang, Wei ;
Huang, Xin ;
Zhang, Wang ;
Li, Huanmin ;
Hu, Chunxiao ;
Tan, Bien .
MACROMOLECULES, 2011, 44 (08) :2410-2414
[26]   Stepwise Crosslinking: A Facile Yet Versatile Conceptual Strategy to Nanomorphology-Persistent Porous Organic Polymers [J].
Liu, Hao ;
Li, Shimei ;
Yang, Hongyu ;
Liu, Shaohong ;
Chen, Luyi ;
Tang, Zhiwei ;
Fu, Ruowen ;
Wu, Dingcai .
ADVANCED MATERIALS, 2017, 29 (27)
[27]  
Ma L, 2011, ACTA CHIM SINICA, V69, P548
[28]  
Mahadevan V, 2002, ANGEW CHEM INT EDIT, V41, P2781, DOI 10.1002/1521-3773(20020802)41:15<2781::AID-ANIE2781>3.0.CO
[29]  
2-S
[30]   Synthesis and characterization of non-aggregating octa-substituted azaphthalocyanines bearing bulky phenoxy substituents [J].
Makhseed, Saad ;
Samuel, Jacob ;
Ibrahim, Fadi .
TETRAHEDRON, 2008, 64 (37) :8871-8877