Simple iron catalyst for terminal alkene epoxidation

被引:127
作者
Dubois, G [1 ]
Murphy, A [1 ]
Stack, TDP [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ol0347085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic A mu-oxo-iron(III) dimer, [((phen)(2)(H2O)Fe-III)(2)(mu-O)](ClO4)(4), is an efficient epoxidation catalyst for a wide range of alkenes, including terminal alkenes, using peracetic acid as the oxidant. Low catalyst loadings, in situ catalyst preparation from common reagents, fast reaction times (<5 min at 0 degreesC), and enhanced reaction performance at high substrate concentrations combine to create a temporally and synthetically efficient procedure for alkene epoxidation.
引用
收藏
页码:2469 / 2472
页数:4
相关论文
共 27 条
[21]   A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions [J].
Sato, K ;
Aoki, M ;
Ogawa, M ;
Hashimoto, T ;
Noyori, R .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8310-8311
[22]  
Swern D., 1970, ORGANIC PEROXIDES, V1
[23]   REGIOSELECTIVE MONOEPOXIDATION OF 1,3-DIENES CATALYZED BY TRANSITION-METAL COMPLEXES [J].
THOMSEN, DS ;
SCHIOTT, B ;
JORGENSEN, KA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (15) :1072-1074
[24]  
VINCENT JM, 1994, TETRAHEDRON LETT, V35, P6287
[25]   A synthetically useful, self-assembling MMO mimic system for catalytic alkene epoxidation with aqueous H2O2 [J].
White, MC ;
Doyle, AG ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (29) :7194-7195
[26]   NONSTEREOSPECIFIC MECHANISMS IN ASYMMETRIC ADDITION TO ALKENES RESULT IN ENANTIODIFFERENTIATION AFTER THE 1ST IRREVERSIBLE STEP [J].
ZHANG, W ;
LEE, NH ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :425-426
[27]  
Zuwei X, 2001, Science, V292, P1139, DOI 10.1126/science.292.5519.1139