Iron-Catalyzed C?H Hydroxylation and Olefin cis-Dihydroxylation Using a Single-Electron Oxidant and Water as the Oxygen-Atom Source

被引:41
作者
Garcia-Bosch, Isaac [1 ]
Codola, Zoel [1 ]
Prat, Irene [1 ]
Ribas, Xavi [1 ]
Lloret-Fillol, Julio [1 ]
Costas, Miquel [1 ]
机构
[1] Univ Girona, Dept Chem, Qbis Grp, Girona 17071, Catalonia, Spain
基金
欧洲研究理事会;
关键词
bioinorganic chemistry; C?H activation; metal-oxo compounds; N ligands; oxidation; water oxidation; ALKANE HYDROXYLATION; DIOXYGEN ACTIVATION; IRIDIUM COMPLEXES; CRYSTAL-STRUCTURE; OXIDATION; OXO; EPOXIDATION; CHEMISTRY; ENZYMES; MODELS;
D O I
10.1002/chem.201202147
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bioinspired oxidation: The hydroxylation of alkanes with retention of the configuration and the cis-dihydroxylation of olefins can be accomplished using [FeII(CF3SO3)2( Me,HPyTACN)] (1) as a catalyst, water as an oxygen-atom source, and cerium ammonium nitrate (CAN) as a single-electron oxidant. The oxidation of C-H bonds and C=C bonds, as well as water oxidation involves a common reaction intermediate formed by the reaction of CAN and [FeIV(O)(OH 2)(Me,HPyTACN)]+. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:13269 / 13273
页数:5
相关论文
共 46 条
[1]  
[Anonymous], 2009, Angew. Chem. Int. Ed, DOI DOI 10.1002/ANGE.200802672
[2]  
[Anonymous], 2006, ANGEW CHEM INT ED, V45, P3446
[3]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P1257
[4]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P3448
[5]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P1803
[6]   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
[7]   Iron(II) complexes with bio-inspired N,N,O ligands as oxidation catalysts:: Olefin epoxidation and cis-dihydroxylation [J].
Bruijnincx, Pieter C. A. ;
Buurmans, Inge L. C. ;
Gosiewska, Silvia ;
Moelands, Marcel A. H. ;
Lutz, Martin ;
Spek, Anthony L. ;
van Koten, Gerard ;
Gebbink, Robertus J. M. Klein .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (04) :1228-1237
[8]   Mononuclear non-heme iron enzymes with the 2-His-1-carboxylate facial triad: recent developments in enzymology and modeling studies [J].
Bruijnincx, Pieter C. A. ;
van Koten, Gerard ;
Gebbink, Robertus J. M. Klein .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (12) :2716-2744
[9]  
Bukowski M.R., 2006, Angew. Chem, V118, P3524
[10]   Radical intermediates in monooxygenase reactions of Rieske dioxygenases [J].
Chakrabarty, Sarmistha ;
Austin, Rachel N. ;
Deng, Dayi ;
Groves, John T. ;
Lipscomb, John D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3514-+