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
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
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
[1]   Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies [J].
Amorati, R ;
Lucarini, M ;
Mugnaini, V ;
Pedulli, GF ;
Minisci, F ;
Recupero, F ;
Fontana, F ;
Astolfi, P ;
Greci, L .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1747-1754
[2]   Aerobic oxidation of benzyl alcohols catalyzed by aryl substituted N-hydroxyphthalimides.: Possible involvement of a charge-transfer complex [J].
Annunziatini, C ;
Gerini, MF ;
Lanzalunga, O ;
Lucarini, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3431-3438
[3]   Catalytic efficiency of natural and synthetic compounds used as laccase-mediators in oxidising veratryl alcohol and a kraft lignin, estimated by electrochemical analysis [J].
Arzola, K. Gonzalez ;
Arevalo, M. C. ;
Falcon, M. A. .
ELECTROCHIMICA ACTA, 2009, 54 (09) :2621-2629
[4]   Nonheme iron complex-catalyzed efficient alcohol oxidation by t-BuOOH with N-hydroxyphthalimide (NHPI) as co-catalyst: Implication of high valent iron-oxo species [J].
Bae, Jeong Mi ;
Lee, Myoung Mi ;
Lee, Seul Ah ;
Lee, Sun Young ;
Bok, Kwon Hee ;
Kim, Jinheung ;
Kim, Cheal .
INORGANICA CHIMICA ACTA, 2016, 451 :8-15
[5]   Promoting laccase activity towards non-phenolic substrates: a mechanistic investigation with some laccase-mediator systems [J].
Baiocco, P ;
Barreca, AM ;
Fabbrini, M ;
Galli, C ;
Gentili, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) :191-197
[6]   Electron Transfer Mechanism in the Oxidation of Aryl 1-Methyl-1-phenylethyl Sulfides Promoted by Nonheme Iron(IV)-Oxo Complexes: The Rate of the Oxygen Rebound Process [J].
Barbieri, Alessia ;
Del Giacco, Tiziana ;
Di Stefano, Stefano ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Mazzonna, Marco ;
Olivo, Giorgio .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12382-12387
[7]   Oxidation of Aryl Diphenylmethyl Sulfides Promoted by a Nonheme Iron(IV)-Oxo Complex: Evidence for an Electron Transfer-Oxygen Transfer Mechanism [J].
Barbieri, Alessia ;
Chimienti, Rosemilia De Carlo ;
Del Giacco, Tiziana ;
Di Stefano, Stefano ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Mazzonna, Marco ;
Olivo, Giorgio ;
Salamone, Michela .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2513-2520
[8]   Isotope effect profiles in the N-demethylation of N,N-dimethylanilines: a key to determine the pKa of nonheme Fe(III)-OH complexes [J].
Barbieri, Alessia ;
De Gennaro, Martina ;
Di Stefano, Stefano ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Mazzonna, Marco ;
Olivo, Giorgio ;
Ticconi, Barbara .
CHEMICAL COMMUNICATIONS, 2015, 51 (24) :5032-5035
[9]   Evaluation of Polar Effects in Hydrogen Atom Transfer Reactions from Activated Phenols [J].
Bietti, Massimo ;
Cucinotta, Erica ;
DiLabio, Gino A. ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Mazzonna, Marco ;
Romero-Montalvo, Eduardo ;
Salamone, Michela .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) :1778-1786
[10]   Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity [J].
Bietti, Massimo ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Martin, Teo ;
Mazzonna, Marco ;
Polin, Mariangela ;
Salamone, Michela .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11) :5761-5768
12345678