Oxidative Decarboxylation of Benzilic Acid by a Biomimetic Iron(II) Complex: Evidence for an Iron(IV)-Oxo-Hydroxo Oxidant from O2

被引:62
作者
Paria, Sayantan [3 ]
Que, Lawrence, Jr. [1 ,2 ]
Paine, Tapan Kanti [3 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
[2] Univ Minnesota, Ctr Met Biocatalysis, Minneapolis, MN 55455 USA
[3] Indian Assoc Cultivat Sci, Dept Inorgan Chem, Kolkata 700032, India
基金
美国国家科学基金会;
关键词
benzilic acid; bioinorganic chemistry; cis-dihydroxylation; iron; oxidative decarboxylation; OLEFIN CIS-DIHYDROXYLATION; OXYGEN ACTIVATION; BENZOATE 1,2-DIOXYGENASE; PSEUDOMONAS-PUTIDA; NONHEME; DIOXYGENASE; BIOSYNTHESIS; CHEMISTRY; CATALYSTS; CLEAVAGE;
D O I
10.1002/anie.201103971
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
O 2-dependent transformation: An iron(II)-benzilate complex of a tridentate N3 donor ligand reacts with O 2 to undergo oxidative decarboxylation. Cyclohexene is selectively converted into cis-cyclohexane-1,2- diol in the reaction. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11129 / 11132
页数:4
相关论文
共 22 条
[1]   SYNTHESIS, STRUCTURE, AND SPECTROSCOPIC PROPERTIES OF COPPER(II) COMPOUNDS CONTAINING NITROGEN SULFUR DONOR LIGANDS - THE CRYSTAL AND MOLECULAR-STRUCTURE OF AQUA[1,7-BIS(N-METHYLBENZIMIDAZOL-2'-YL)-2,6-DITHIAHEPTANE]COPPER(II) PERCHLORATE [J].
ADDISON, AW ;
RAO, TN ;
REEDIJK, J ;
VANRIJN, J ;
VERSCHOOR, GC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (07) :1349-1356
[2]   Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts:: Two faces of an FeIII-OOH coin [J].
Chen, K ;
Costas, M ;
Kim, JH ;
Tipton, AK ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :3026-3035
[3]   An unusual carbon-carbon bond cleavage reaction during phosphinothricin biosynthesis [J].
Cicchillo, Robert M. ;
Zhang, Houjin ;
Blodgett, Joshua A. V. ;
Whitteck, John T. ;
Li, Gongyong ;
Nair, Satish K. ;
van der Donk, Wilfred A. ;
Metcalf, William W. .
NATURE, 2009, 459 (7248) :871-U10
[4]   Olefin-Dependent Discrimination between Two Nonheme HO-FeV=O Tautomeric Species in Catalytic H2O2 Epoxidations [J].
Company, Anna ;
Feng, Yan ;
Guell, Mireia ;
Ribas, Xavi ;
Luis, Josep M. ;
Que, Lawrence, Jr. ;
Costas, Miquel .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3359-3362
[5]   Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates [J].
Costas, M ;
Mehn, MP ;
Jensen, MP ;
Que, L .
CHEMICAL REVIEWS, 2004, 104 (02) :939-986
[6]   Crystal structure of naphthalene dioxygenase: Side-on binding of dioxygen to iron [J].
Karlsson, A ;
Parales, JV ;
Parales, RE ;
Gibson, DT ;
Eklund, H ;
Ramaswamy, S .
SCIENCE, 2003, 299 (5609) :1039-1042
[7]   Versatility of biological non-heme Fe(II) centers in oxygen activation reactions [J].
Kovaleva, Elena G. ;
Lipscomb, John D. .
NATURE CHEMICAL BIOLOGY, 2008, 4 (03) :186-193
[8]   Oxygen activation by nonheme iron(II) complexes:: α-keto carboxylate versus carboxylate [J].
Mehn, MP ;
Fujisawa, K ;
Hegg, EL ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7828-7842
[9]  
MUKHERJEE A, 2009, ANGEW CHEM, V121, P1812
[10]   Oxygen Activation at Mononuclear Nonheme Iron Centers: A Superoxo Perspective [J].
Mukherjee, Anusree ;
Cranswick, Matthew A. ;
Chakrabarti, Mrinmoy ;
Paine, Tapan K. ;
Fujisawa, Kiyoshi ;
Muenck, Eckard ;
Que, Lawrence, Jr. .
INORGANIC CHEMISTRY, 2010, 49 (08) :3618-3628