Development of a general and efficient iron-catalyzed epoxidation with hydrogen peroxide as oxidant

被引:66
作者
Bitterlich, Bianca
Anilkumar, Gopinathan
Gelalcha, Feyissa Gadissa
Spilker, Bjoern
Grotevendt, Anne
Jackstell, Ralf
Tse, Man Kin
Beller, Matthias
机构
[1] Leibniz Inst Katalyse, D-18059 Rostock, Germany
[2] Univ Rostock, Ctr Life Sci Automat, D-18119 Rostock, Germany
关键词
alkenes; epoxidation; homogeneous catalysis; hydrogen peroxide; iron;
D O I
10.1002/asia.200600407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of inexpensive and practical iron catalysts for the environmentally benign epoxidation of olefins with hydrogen peroxide as terminal oxidant is described. By systematic variation of ligands, metal sources, and reaction conditions, it was discovered that FeCl3 center dot 6H(2)O in combination with pyridine-2,6-dicarboxylic acid and different amines shows high reactivity and excellent selectivity towards the epoxidation of aromatic olefins and moderate reactivity towards that of aliphatic olefins.
引用
收藏
页码:521 / 529
页数:9
相关论文
共 66 条
[1]   A highly chemoselective, diastereoselective, and regioselective epoxidation of chiral allylic alcohols with hydrogen peroxide, catalyzed by sandwich-type polyoxometalates:: Enhancement of reactivity and control of selectivity by the hydroxy group through metal-alcoholate bonding [J].
Adam, W ;
Alsters, PL ;
Neumann, R ;
Saha-Möller, CR ;
Sloboda-Rozner, D ;
Zhang, R .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1721-1728
[2]   Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations [J].
Anilkumar, G ;
Bhor, S ;
Tse, MK ;
Klawonn, M ;
Bitterlich, B ;
Beller, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (21) :3536-3561
[3]   An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide [J].
Anilkumar, Gopinathan ;
Bitterlich, Bianca ;
Gelalcha, Feyissa Gadissa ;
Tse, Man Kin ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2007, (03) :289-291
[4]   Recent developments in selective catalytic epoxidations with H2O2 [J].
Arends, IWCE ;
Sheldon, RA .
TOPICS IN CATALYSIS, 2002, 19 (01) :133-141
[5]   Models for non-heme oxidation enzymes [J].
Barton, DHR ;
Taylor, DK .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :497-504
[6]   The selective functionalization of saturated hydrocarbons: recent developments in Gif chemistry [J].
Barton, DHR ;
Hu, B .
PURE AND APPLIED CHEMISTRY, 1997, 69 (09) :1941-1950
[7]   A density functional study of O-O bond cleavage for a biomimetic non-heme iron complex demonstrating an FeV-intermediate [J].
Bassan, A ;
Blomberg, MRA ;
Siegbahn, PEM ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :11056-11063
[8]  
Beller M., 1998, TRANSITION METALS OR, V2, P157
[9]   Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation [J].
Bhor, S ;
Anilkumar, G ;
Tse, MK ;
Klawonn, M ;
Dobler, C ;
Bitterlich, B ;
Grotevendt, A ;
Beller, M .
ORGANIC LETTERS, 2005, 7 (16) :3393-3396
[10]   Ruthenium-catalyzed asymmetric alkene epoxidation with tert-butyl hydroperoxide as oxidant [J].
Bhor, S ;
Tse, MK ;
Klawonn, M ;
Döbler, C ;
Mägerlein, WB ;
Beller, M .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :263-267