New immobilized chiral Mn(III) salen complexes on pyridine N-oxide-modified MCM-41 as effective catalysts for epoxidation of nonfunctionalized alkenes

被引：89

作者：

Kureshy, RI ^{[1
]}

Ahmad, I ^{[1
]}

Khan, NUH ^{[1
]}

Abdi, SHR ^{[1
]}

Singh, S ^{[1
]}

Pandia, PH ^{[1
]}

Jasra, RV ^{[1
]}

机构：

[1] Cent Salt & Marine Chem Res Inst, Silicates & Catalysis Discipline, Bhavnagar 364002, Gujarat, India

来源：

JOURNAL OF CATALYSIS | 2005年 / 235卷 / 01期

关键词：

enantioselective epoxidation; modified MCM-41; nonfunctionalized alkenes; chiral Mn(III) salen complexes;

D O I：

10.1016/j.jcat.2004.11.002

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：

We prepared new chiral Mn(III) salen complexes 1'-4' immobilized on pyridine N-oxide-modified MCM-41 through the axial coordination. Epoxidation of styrene and 4-chlorostyrene with the use of these complexes as catalysts in the presence of NaOCl was found to proceed enantioselectively (ee, 62-69%) at 0 degrees C in 8-12 h, which is a significantly higher enantioselectivity than that observed for their homogeneous counterparts (ee, 36-51%). These catalysts were also effective for the relatively bulkier alkenes, such as indene and 2,2-dimethylchromene, and have shown a reactivity (82-98%) and an enantioselectivity (69-92%) similar to those observed for their homogeneous system. The catalysts could be recycled several times without loss of performance. (c) 2004 Published by Elsevier Inc.

引用

页码：28 / 34

页数：7

共 33 条

[21] PERRIN DD, 1981, PURIFICATION LAB CHE
[22] Enantioselective epoxidation of (Z)-stilbene using a chiral Mn(III)-salen complex:: effect of immobilisation on MCM-41 on product selectivity
Piaggio, P
McMorn, P
Murphy, D
Bethell, D
Page, PCB
Hancock, FE
Sly, C
Kerton, OJ
Hutchings, GJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (10): : 2008 - 2015
[23] Polymer-supported (salen)Mn catalysts for asymmetric epoxidation: A comparison between soluble and insoluble matrices
Reger, TS
Janda, KD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) : 6929 - 6934
[24] Asymmetric epoxidation using a singly-bound supported Katsuki-type (salen) Mn complex
Smith, K
Liu, CH
[J]. CHEMICAL COMMUNICATIONS, 2002, (08) : 886 - 887
[25] Supported chiral catalysts on inorganic materials
Song, CE
Lee, SG
[J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3495 - 3524
[26] Practical method to recycle a chiral (salen)Mn epoxidation catalyst by using an ionic liquid
Song, CE
Roh, EJ
[J]. CHEMICAL COMMUNICATIONS, 2000, (10) : 837 - 838
[27] Heterogeneous asymmetric epoxidation of alkenes catalysed by a polymer-bound (pyrrolidine salen)manganese(III) complex
Song, CE
Roh, EJ
Yu, BM
Chi, DY
Kim, SC
Lee, KJ
[J]. CHEMICAL COMMUNICATIONS, 2000, (07) : 615 - 616
[28] Chiral catalytic membranes
Vankelecom, IFJ
Tas, D
Parton, RF
VandeVyver, V
Jacobs, PA
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (12): : 1346 - 1348
[29] Enantioselective epoxidation of olefins catalyzed by Mn (salen)/MCM-41 synthesized with a new anchoring method
Xiang, S
Zhang, YL
Xin, Q
Li, C
[J]. CHEMICAL COMMUNICATIONS, 2002, (22) : 2696 - 2697
[30] Ying JY, 1999, ANGEW CHEM INT EDIT, V38, P56, DOI 10.1002/(SICI)1521-3773(19990115)38:1/2<56::AID-ANIE56>3.0.CO

← 1 2 3 4 →