N-Hydroxyphthalimide: A Hydrogen Atom Transfer Mediator in Hydrocarbon Oxidations Promoted by Nonheme Iron(IV)-Oxo Complexes

被引:26
作者
Barbieri, Alessia [1 ]
Lanzalunga, Osvaldo [1 ]
Lapi, Andrea [1 ]
Di Stefano, Stefano [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, Ist CNR & Sistemi Biol ISB CNR, Sez Meccanismi Reaz, Ple A Moro 5, I-00185 Rome, Italy
关键词
COUPLED ELECTRON-TRANSFER; C-H; IRON CATALYSTS; NONPHENOLIC LIGNIN; AEROBIC OXIDATION; LACCASE-MEDIATORS; MOLECULAR-OXYGEN; ANODIC-OXIDATION; BENZYL ALCOHOLS; BOND-CLEAVAGE;
D O I
10.1021/acs.joc.9b01813
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidation of a series of hydrocarbons by the nonheme iron(IV)-oxo complex [(N4Py)Fe-IV=O](2+) is efficiently mediated by N-hydroxyphthalimide. The increase of reactivity is associated to the oxidation of the mediator to the phthalimide N-oxyl radical, which efficiently abstracts a hydrogen atom from the substrates, regenerating the mediator in its reduced form.
引用
收藏
页码:13549 / 13556
页数:8
相关论文
共 78 条
[11]   Redox Catalysis Facilitates Lignin Depolymerization [J].
Bosque, Irene ;
Magallanes, Gabriel ;
Rigoulet, Mathilde ;
Karkas, Markus D. ;
Stephenson, Corey R. J. .
ACS CENTRAL SCIENCE, 2017, 3 (06) :621-628
[12]   Reactivities of various mediators and laccases with kraft pulp and lignin model compounds [J].
Bourbonnais, R ;
Paice, MG ;
Freiermuth, B ;
Bodie, E ;
Borneman, S .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1997, 63 (12) :4627-4632
[13]   Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid [J].
Cai, Y ;
Koshino, N ;
Saha, B ;
Espenson, JH .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :238-243
[14]   Coupled X-ray Absorption/UV-vis Monitoring of Fast Oxidation Reactions Involving a Nonheme Iron-Oxo Complex [J].
Capocasa, Giorgio ;
Sessa, Francesco ;
Tavani, Francesco ;
Monte, Manuel ;
Olivo, Giorgio ;
Pascarelli, Sakura ;
Lanzalunga, Osvaldo ;
Di Stefano, Stefano ;
D'Angelo, Paola .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (06) :2299-2304
[15]   Stereospecific alkane hydroxylation by non-heme iron catalysts:: Mechanistic evidence for an FeV=O active species [J].
Chen, K ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6327-6337
[16]   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
[17]   Metal-free allylic/benzylic oxidation strategies with molecular oxygen: recent advances and future prospects [J].
Chen, Kexian ;
Zhang, Pengfei ;
Wang, Yong ;
Li, Haoran .
GREEN CHEMISTRY, 2014, 16 (05) :2344-2374
[18]   A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2007, 318 (5851) :783-787
[19]   Evidence for an Alternative to the Oxygen Rebound Mechanism in C-H Bond Activation by Non-Heme FeIVO Complexes [J].
Cho, Kyung-Bin ;
Wu, Xiujuan ;
Lee, Yong-Min ;
Kwon, Yoon Hye ;
Shaik, Sason ;
Nam, Wonwoo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (50) :20222-20225
[20]   Electrochemical generation of a nonheme oxoiron(IV) complex [J].
Collins, Michael J. ;
Ray, Kallol ;
Que, Lawrence, Jr. .
INORGANIC CHEMISTRY, 2006, 45 (20) :8009-8011