Fe2+-catalyzed heterolytic RO-OH bond cleavage and substrate oxidation:: A functional synthetic non-heme iron monooxygenase system

被引:57
作者
Foster, TL [1 ]
Caradonna, JP [1 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
关键词
D O I
10.1021/ja0286268
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of [Fe22+(H2Hbamb)2(N-MeIm)2], [1], a binuclear, non-heme iron complex, with 2-methyl-1-phenylprop-2-yl hydroperoxide (MPPH) shows that [1] induces heterolytic cleavage of the peroxy O-O bond. Catalytic atom transfer reactions (1:MPPH:PhSMe 1:596:6011) resulted in the highly efficient (99 ± 1%), catalytic oxidation of phenyl methyl sulfide to phenyl methyl sulfoxide/sulfone (T.N. = 500/11 respectively) and cyclohexane to cyclohexanol/cyclohexanone (T.N. = 230/5 respectively) showing the highly efficient, catalytic capacity of [1] to carry out oxygen insertion chemistry. Copyright © 2003 American Chemical Society.
引用
收藏
页码:3678 / 3679
页数:2
相关论文
共 13 条
[1]   A MECHANISTIC PROBE FOR OXYGEN ACTIVATION BY METAL-COMPLEXES AND HYDROPEROXIDES AND ITS APPLICATION TO ALKANE FUNCTIONALIZATION BY [FE(III)CL(2)TRIS(2-PYRIDINYLMETHYL)AMINE](+)BF4- [J].
ARENDS, IWCE ;
INGOLD, KU ;
WAYNER, DDM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4710-4711
[2]  
Christian Gary D, 1994, ANAL CHEM
[3]  
GERALD K, 1995, J AM CHEM SOC, V117, P7139
[4]  
HIATT RR, 1963, J AM CHEM SOC, V2, P1803
[5]   SPECTROMETRIC ASSAY OF ALDEHYDES AS 6-MERCAPTO-3-SUBSTITUTED-S-TRIAZOLO(4,3-B)-S-TETRAZINES [J].
JACOBSEN, NW ;
DICKINSON, RG .
ANALYTICAL CHEMISTRY, 1974, 46 (02) :298-299
[6]   Pterin-dependent amino acid hydroxylases [J].
Kappock, TJ ;
Caradonna, JP .
CHEMICAL REVIEWS, 1996, 96 (07) :2659-2756
[7]   A putative monooxygenase mimic which functions via well-disguised free radical chemistry [J].
MacFaul, PA ;
Ingold, KU ;
Wayner, DDM ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10594-10598
[8]  
MACFAUL PA, 1997, J CHEM SOC P2, V2, P135
[9]   ENZYMOLOGY OF OXYGEN [J].
MALMSTROM, BG .
ANNUAL REVIEW OF BIOCHEMISTRY, 1982, 51 :21-59
[10]  
MUCKERJEE S, 1997, J AM CHEM SOC, V119, P8097