Electrocatalytic Aziridination of Alkenes Mediated by n-Bu4NI: A Radical Pathway

被引：139

作者：

Chen, Jie ^{[1
]}

Yan, Wei-Qing ^{[1
]}

Lam, Chiu Marco ^{[2
]}

Zeng, Cheng-Chu ^{[1
]}

Hu, Li-Ming ^{[1
]}

Little, R. Daniel ^{[2
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

[2] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

METAL-FREE AZIRIDINATION; CATALYZED AZIRIDINATION; CHLORAMINE-T; OLEFINS; IODINE;

D O I：

10.1021/acs.orglett.5b00083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient electrocatalytic aziridination of alkenes has been achieved for the first time. A structurally broad range of aziridines was easily accessed using an undivided cell operated at constant current and mediated by a catalytic quantity of n-Bu4NI. The electrocatalytic reaction also proceeded in the absence of additional conducting salt. The aziridination is proposed to follow a radical mechanism.

引用

页码：986 / 989

页数：4

共 33 条

[1] Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source [J].

Ando, T ;

Kano, D ;

Minakata, S ;

Ryu, I ;

Komatsu, M .

TETRAHEDRON, 1998, 54 (44) :13485-13494

[2] Characteristics of the Iodide/Triiodide Redox Mediator in Dye-Sensitized Solar Cells [J].

Boschloo, Gerrit ;

Hagfeldt, Anders .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1819-1826

[3] Optimizing Electron Transfer Mediators Based on Arylimidazoles by Ring Fusion: Synthesis, Electrochemistry, and Computational Analysis of 2-Aryl-1-methylphenanthro[9,10-d]imidazoles [J].

Francke, Robert ;

Little, R. Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :427-435

[4]

Gao W. J., 2015, J ORG CHEM, V80, P781

[5] Visible Light Generation of Iodine Atoms and I-I Bonds: Sensitized I- Oxidation and I3- Photodissociation [J].

Gardner, James M. ;

Abrahamsson, Maria ;

Farnum, Byron H. ;

Meyer, Gerald J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) :16206-16214

[6] An efficient transition metal-free aziridination of alkenes with chloramine-T using aqueous H2O2/HBr [J].

Jain, SL ;

Sharma, VB ;

Sain, B .

TETRAHEDRON LETTERS, 2004, 45 (47) :8731-8732

[7] Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element [J].

Jeong, JU ;

Tao, B ;

Sagasser, I ;

Henniges, H ;

Sharpless, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (27) :6844-6845

[8] New Catalysts for the Transition-Metal-Catalyzed Synthesis of Aziridines [J].

Jung, Nicole ;

Braese, Stefan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (23) :5538-5540

[9] Metal-Free Aziridination of Styrene Derivatives with Iminoiodinane Catalyzed by a Combination of Iodine and Ammonium Iodide [J].

Kiyokawa, Kensuke ;

Kosaka, Tomoki ;

Minakata, Satoshi .

ORGANIC LETTERS, 2013, 15 (18) :4858-4861

[10] Highly regioselective transformation of alkenyl bromides into α-bromoaziridines and α-bromohydrazones [J].

Krasnova, LB ;

Yudin, AK .

ORGANIC LETTERS, 2006, 8 (10) :2011-2014

← 1 2 3 4 →