Aryl iodide mediated aziridination of alkenes

被引：68
作者：
Li, JY
Chan, PWH
Che, CM
机构：
[1] Acad Sinica, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
[2] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[3] Univ Hong Kong, Open Lab Chem Biol, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 26期
关键词：
D O I：
10.1021/ol052293c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K(2)CO(3), CH(2)Cl(2), 25 degrees C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.
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页码：5801 / 5804
页数：4
相关论文
共 53 条
[1]  
[Anonymous], 2003, HYPERVALENT IODINE C
[2]   3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines [J].
Atkinson, RS .
TETRAHEDRON, 1999, 55 (06) :1519-1558
[3]   AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES [J].
ATKINSON, RS ;
GRIMSHIRE, MJ ;
KELLY, BJ .
TETRAHEDRON, 1989, 45 (10) :2875-2886
[4]   EVIDENCE FOR PHTHALIMIDONITRENE AS A COMMON INTERMEDIATE IN SEVERAL EXTRUSION REACTIONS [J].
ATKINSON, RS ;
JONES, DW ;
KELLY, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1344-1346
[5]   STEREOSELECTIVITY IN ADDITION OF N-NITRENES TO OLEFINS [J].
ATKINSON, RS ;
MALPASS, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20) :2242-2249
[6]   Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].
Au, SM ;
Huang, JS ;
Yu, WY ;
Fung, WH ;
Che, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132
[7]   Ruthenium-mediated amidation of saturated C-H bonds and crystal structure of a bis(tosyl)amidoruthenium(III) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane [J].
Au, SM ;
Zhang, SB ;
Fung, WH ;
Yu, WY ;
Che, CM ;
Cheung, KK .
CHEMICAL COMMUNICATIONS, 1998, (24) :2677-2678
[8]  
Breslow R., 1982, CHEM COMMUN, P1400
[9]   Preparation and ring-opening reactions of N-diphenylphosphinyl aziridines [J].
Cantrill, AA ;
Osborn, HMI ;
Sweeney, J .
TETRAHEDRON, 1998, 54 (10) :2181-2208
[10]   Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate [J].
Catino, AJ ;
Nichols, JM ;
Forslund, RE ;
Doyle, MP .
ORGANIC LETTERS, 2005, 7 (13) :2787-2790
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