Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis

被引:312
作者
Bergbreiter, David E. [1 ]
Tian, Jianhua [1 ]
Hongfa, Chayanant [1 ]
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
基金
美国国家科学基金会;
关键词
PHASE-TRANSFER LIGANDS; HYDROLYTIC KINETIC RESOLUTION; SUPERCRITICAL CARBON-DIOXIDE; CROSS-LINKED POLYSTYRENE; POLY(ETHYLENE GLYCOL)-SUPPORTED TEMPO; HIGHLY ENANTIOSELECTIVE EPOXIDATION; STABILIZED PALLADIUM NANOPARTICLES; FLUOROUS BIPHASE HYDROFORMYLATION; ASYMMETRIC TRANSFER HYDROGENATION; END-FUNCTIONALIZED POLYSTYRENES;
D O I
10.1021/cr8004235
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review of various research studies conducted since 2002 on the use of soluble polymer supports to facilitate homogeneous catalysis is presented. TEMPO is a commonly used organocatalyst for the selective oxidation of primary alcohols to aldehydes. Use of PEG-supported proline as a catalyst is described in enantioselective conjugate addition reactions. A phosphonium salt is described and is found to deliver catalyzed formation of cyclic carbonates, while intermediate cyclic carbonates could be used without isolation as a phosgene-equivalent. The synthesis of three types of PEG-supported salen ligands could be used to catalyze the addition of diethyl zinc to aldehydes. A study including the use of PEG supports to prepare a tartate ester library is an effort to probe the effect of tartrate structure on stereoselectivity in Sharpless asymmetric epoxidation of allylic alcohols.
引用
收藏
页码:530 / 582
页数:53
相关论文
共 308 条
[11]   Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation [J].
Bandini, Marco ;
Benaglia, Maurizio ;
Sinisi, Riccardo ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
ORGANIC LETTERS, 2007, 9 (11) :2151-2153
[12]   New recoverable poly(ethylene glycol)-supported C1-diamino-oligothiophene ligands for palladium-promoted asymmetric allylic alkylation (AAA) reactions [J].
Bandini, Marco ;
Benaglia, Maurizio ;
Quinto, Tommaso ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1521-1527
[13]   Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen [J].
Barder, Timothy E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5096-5101
[14]   Closer to the "ideal recoverable catalyst" for atom transfer radical polymerization using a molecular non-fluorous thermomorphic system [J].
Barré, G ;
Taton, D ;
Lastcouères, D ;
Vincent, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7764-7765
[15]   A soluble-polymer system for the asymmetric transfer hydrogenation of ketones [J].
Bastin, S ;
Eaves, RJ ;
Edwards, CW ;
Ichihara, O ;
Whittaker, M ;
Wills, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5405-5412
[16]   LIQUID-PHASE SYNTHESIS OF PEPTIDES [J].
BAYER, E ;
MUTTER, M .
NATURE, 1972, 237 (5357) :512-&
[17]  
Bayer E.A., 1986, CHEM PEPT PROTEINS, V3, P3
[18]   Thermoregulated liquid/liquid catalyst separation and recycling [J].
Behr, Arno ;
Henze, Guido ;
Schomaecker, Reinhard .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1485-1495
[19]   Poly(N-vinylimidazole) as efficient and recyclable catalyst for the addition of thiols to michael acceptors in aqueous medium [J].
Beletskaya, I. P. ;
Tarasenko, E. A. ;
Khokhlov, A. R. ;
Tyurin, V. S. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (11) :1733-1736
[20]   Palladium colloid stabilized by block copolymer micelles as an efficient catalyst for reactions of C-C and C-heteroatom bond formation [J].
Beletskaya, IP ;
Kashin, AN ;
Litvinov, AE ;
Tyurin, VS ;
Valetsky, PM ;
van Koten, G .
ORGANOMETALLICS, 2006, 25 (01) :154-158