Well-Defined Silica-Supported Olefin Metathesis Catalysts

被引：108

作者：

Allen, Daryl P. ^{[1
]}

Van Wingerden, Matthew M. ^{[1
]}

Grubbs, Robert H. ^{[1
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

RING-CLOSING METATHESIS; N-HETEROCYCLIC CARBENE; TETRASUBSTITUTED OLEFINS; DECOMPOSITION; COMPLEXES; REACTIVITY; EFFICIENT; LIGANDS;

D O I：

10.1021/ol9000153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two triethoxysilyl-functionalized N-heterocyclic carbene ligands have been synthesized and used to prepare the corresponding second-generation ruthenium olefin metathesis catalysts. These complexes were then grafted onto silica gel, and the resulting materials were efficient heterogeneous catalysts for a number of metathesis reactions. The solid-supported catalysts were shown to be recyclable over a number of reaction cycles, and no detectable levels of ruthenium were observed in reaction filtrates (ruthenium concentration of filtrate <5 ppb).

引用

页码：1261 / 1264

页数：4

共 42 条

[1] Deactivation of ruthenium metathesis catalysts via facile formation of face-bridged dimers [J].

Amoroso, D ;

Yap, GPA ;

Fogg, DE .

ORGANOMETALLICS, 2002, 21 (16) :3335-3343

[2]

Amoroso D, 2002, ADV SYNTH CATAL, V344, P757, DOI 10.1002/1615-4169(200208)344:6/7<757::AID-ADSC757>3.0.CO

[3]

2-X

[4] Synthesis and reactivity of olefin metathesis catalysts bearing cyclic (alkyl) (amino) carbenes [J].

Anderson, Donde R. ;

Lavallo, Vincent ;

O'Leary, Daniel J. ;

Bertrand, Guy ;

Grubbs, Robert H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7262-7265

[5] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].

Annis, DA ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154

[6] Ruthenium-catalyzed ring-closing metathesis to form tetrasubstituted olefins [J].

Berlin, Jacob M. ;

Campbell, Katie ;

Ritter, Tobias ;

Funk, Timothy W. ;

Chlenov, Anatoly ;

Grubbs, Robert H. .

ORGANIC LETTERS, 2007, 9 (07) :1339-1342

[7] Recent advances in the synthesis of supported metathesis catalysts [J].

Buchmeiser, MR .

NEW JOURNAL OF CHEMISTRY, 2004, 28 (05) :549-557

[8] Olefin metathesis catalyst: Stabilization effect of backbone substitutions of N-heterocyclic carbene [J].

Chung, Cheol K. ;

Grubbs, Robert H. .

ORGANIC LETTERS, 2008, 10 (13) :2693-2696

[9] Sustainable concepts in olefin metathesis [J].

Clavier, Herve ;

Grela, Karo ;

Kirschning, Andreas ;

Mauduit, Marc ;

Nalon, Steven P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) :6786-6801

[10] A SILICA-SUPPORTED RHODIUM HYDROFORMYLATION CATALYST - EVIDENCE FOR DINUCLEAR ELIMINATION [J].

COLLMAN, JP ;

BELMONT, JA ;

BRAUMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (25) :7288-7294

← 1 2 3 4 5 →