Copper-Catalyzed Aziridination with Redox-Active Ligands: Molecular Spin Catalysis

被引：31

作者：

Ren, Yufeng ^{[1
]}

Cheaib, Khaled ^{[1
]}

Jacquet, Jeremy ^{[1
]}

Vezin, Herve ^{[2
]}

Fensterbank, Louis ^{[1
]}

Orio, Maylis ^{[3
]}

Blanchard, Sebastien ^{[1
]}

Desage-El Murr, Marine ^{[1
,4
]}

机构：

[1] Univ Paris 06, Sorbonne Univ, UMR CNRS 8232, UPMC,Inst Parisien Chim Mol, Paris, France

[2] Univ Lille, CNRS UMR 8516, Lab Spectrochim Infrarouge & Raman, F-59000 Lille, France

[3] Aix Marseille Univ, CNRS, Cent Marseille, UMR iSm2 7313, F-13397 Marseille 20, France

[4] Univ Strasbourg, Inst Chim, 1 Rue Blaise Pascal, F-67000 Strasbourg, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 20期

关键词：

aziridination; copper catalysis; multistate reactivity; redox-active ligands; spin catalysis; NITRENE TRANSFER-REACTIONS; NON-INNOCENT LIGANDS; RADICAL LIGANDS; ALKENE AZIRIDINATION; AEROBIC OXIDATION; METAL REACTIVITY; COMPLEX; CYTOCHROME-P450; HYDROXYLATION; EPOXIDATION;

D O I：

10.1002/chem.201705649

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Small-molecule catalysts as mimics of biological systems illustrate the chemists' attempts at emulating the tantalizing abilities displayed by nature's metalloenzymes. Among these innate behaviors, spin multistate reactivity is used by biological systems as it offers thermodynamic leverage towards challenging chemical reactivity but this concept is difficult to translate into the realm of synthetic organometallic catalysis. Here, we report a rare example of molecular spin catalysis involving multistate reactivity in a small-molecule biomimetic copper catalyst applied to aziridination. This behavior is supported by spin state flexibility enabled by the redox-active ligand.

引用

页码：5086 / 5090

页数：5

共 50 条

[1] Copper catalysis with redox-active ligands
Das, Agnideep
Ren, Yufeng
Hessin, Cheriehan
Desage-El Murr, Marine
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 858 - 870
[2] Redox-Active Ligands in Catalysis
Praneeth, Vijayendran K. K.
Ringenberg, Mark R.
Ward, Thomas R.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) : 10228 - 10234
[3] Redox-active ligands in catalysis
Luca, Oana R.
Crabtree, Robert H.
CHEMICAL SOCIETY REVIEWS, 2013, 42 (04) : 1440 - 1459
[4] Copper-Catalyzed Decarboxylative Radical Silylation of Redox-Active Aliphatic Carboxylic Acid Derivatives
Xue, Weichao
Oestreich, Martin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (38) : 11649 - 11652
[5] Copper-catalyzed enantioselective aziridination of styrenes
Lebel, Helene
Parmentier, Michael
PURE AND APPLIED CHEMISTRY, 2010, 82 (09) : 1827 - 1833
[6] Copper-catalyzed aziridination of allylglycine derivatives
Leman, L
Sanière, L
Dauban, P
Dodd, RH
ARKIVOC, 2003, : 126 - 134
[7] Synthesis of transition metal complexes with redox-active ligands for catalysis
Stone, Kari L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[8] Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters
Lu, Xiao-Yu
Gao, Ang
Liu, Qi-Le
Xia, Ze-Jie
TETRAHEDRON, 2021, 92
[9] Deciphering the active species and reaction mechanism in water oxidation catalyzed by a copper complex with redox-active ligands
Fan, Qing
Yang, Cong
Li, Mengdi
Wang, Chen
Wang, Guixia
Kong, Xiangfei
Zhu, Qiping
INORGANIC CHEMISTRY FRONTIERS, 2024, 11 (08) : 2365 - 2372
[10] DEVELOPMENT OF THE COPPER-CATALYZED OLEFIN AZIRIDINATION REACTION
EVENS, DA
FAUL, MM
BILODEAU, MT
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 2742 - 2753

← 1 2 3 4 5 →