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
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.
引用
收藏
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
    Atkinson, RS
    [J]. TETRAHEDRON, 1999, 55 (06) : 1519 - 1558
  • [3] AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES
    ATKINSON, RS
    GRIMSHIRE, MJ
    KELLY, BJ
    [J]. TETRAHEDRON, 1989, 45 (10) : 2875 - 2886
  • [4] EVIDENCE FOR PHTHALIMIDONITRENE AS A COMMON INTERMEDIATE IN SEVERAL EXTRUSION REACTIONS
    ATKINSON, RS
    JONES, DW
    KELLY, BJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1344 - 1346
  • [5] STEREOSELECTIVITY IN ADDITION OF N-NITRENES TO OLEFINS
    ATKINSON, RS
    MALPASS, JR
    [J]. 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
    Au, SM
    Huang, JS
    Yu, WY
    Fung, WH
    Che, CM
    [J]. 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
    Au, SM
    Zhang, SB
    Fung, WH
    Yu, WY
    Che, CM
    Cheung, KK
    [J]. CHEMICAL COMMUNICATIONS, 1998, (24) : 2677 - 2678
  • [8] Breslow R., 1982, CHEM COMMUN, P1400
  • [9] Preparation and ring-opening reactions of N-diphenylphosphinyl aziridines
    Cantrill, AA
    Osborn, HMI
    Sweeney, J
    [J]. TETRAHEDRON, 1998, 54 (10) : 2181 - 2208
  • [10] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate
    Catino, AJ
    Nichols, JM
    Forslund, RE
    Doyle, MP
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2787 - 2790