In Situ Generation of the Coates Catalyst: A Practical and Versatile Catalytic System for the Carbonylation of meso-Epoxides

被引:28
作者
Ganji, Prasad [1 ]
Doyle, David J. [1 ]
Ibrahim, Hasim [1 ]
机构
[1] Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland
基金
爱尔兰科学基金会;
关键词
BETA-LACTONE SYNTHESIS; DICOBALT OCTACARBONYL; INDUCED DISPROPORTIONATION; ASYMMETRIC-SYNTHESIS; TERMINAL EPOXIDES; COBALT; ACID; CARBOMETHOXYLATION; COMPLEXES; CATIONS;
D O I
10.1021/ol201043d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly active catalytic system for the carbonylation of meso- and terminal epoxides to beta-lactones is described. The active catalyst, analogous to Coates' catalyst, is generated in situ from commercially available (TPP)CrCl and Co(2)(CO)(8). This practical system circumvents the prepaiation of air sensitive cobaltate salts, operates at low catalyst loadings, and allows the carbonylation of functionalized, sterically demanding and heterocyclic meso-epoxides.
引用
收藏
页码:3142 / 3145
页数:4
相关论文
共 35 条
[1]   THE MECHANISM OF SUBSTITUTION OF DICOBALT OCTACARBONYL [J].
ABSIHALABI, M ;
ATWOOD, JD ;
FORBUS, NP ;
BROWN, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (20) :6248-6254
[2]   Hydrogen Peroxide or Peracetic Acid Mediated Self-Titrating α-Halogenation of 1,3-Dicarbonyl Compounds [J].
Akula, Ramulu ;
Galligan, Marc J. ;
Ibrahim, Hasim .
SYNTHESIS-STUTTGART, 2011, (02) :347-351
[3]   Umpolung of halide reactivity: efficient (diacetoxyiodo)benzene-mediated electrophilic α-halogenation of 1,3-dicarbonyl compounds [J].
Akula, Ramulu ;
Galligan, Marc ;
Ibrahim, Hasim .
CHEMICAL COMMUNICATIONS, 2009, (45) :6991-6993
[4]   Cobaltcarbonyl complexes - Tunable catalysts for the carbonylation of epoxides [J].
Allmendinger, M ;
Eberhardt, R ;
Luinstra, GA ;
Molnar, F ;
Rieger, B .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2003, 629 (7-8) :1347-1352
[5]  
[Anonymous], [No title captured], Patent No. 577206
[6]   HALIDE ION-INDUCED DISPROPORTIONATION OF COBALT CARBONYLS - FORMATION OF [CO(CO)4]- AND SUBSEQUENT CYCLIC KETONE SYNTHESIS [J].
BRATERMAN, PS ;
WALKER, BS ;
ROBERTSON, TH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (18) :651-652
[7]   STRONG-INTERACTIONS BETWEEN [CO(CO)4]- AND LI+ OR NA+ IN DIETHYL-ETHER - THE SYSTEM LIBR-CO2(CO)8-DIETHYL ETHER [J].
BRATERMAN, PS ;
LESLIE, AE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 214 (03) :C45-C49
[8]   Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid [J].
Bunnage, ME ;
Davies, SG ;
Roberts, PM ;
Smith, AD ;
Withey, JM .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2763-2776
[9]   Binding of propylene oxide to porphyrin- and salen-M(III) cations, where M = Al, Ga, Cr, and Co [J].
Chen, P ;
Chisholm, MH ;
Gallucci, JC ;
Zhang, XY ;
Zhou, ZP .
INORGANIC CHEMISTRY, 2005, 44 (08) :2588-2595
[10]   Carbonylation of heterocycles by homogeneous catalysts [J].
Church, Tamara L. ;
Getzler, Yutan D. Y. L. ;
Byrne, Christopher M. ;
Coates, Geoffrey W. .
CHEMICAL COMMUNICATIONS, 2007, (07) :657-674