Copper-Catalyzed Intermolecular Aminoazidation of Alkenes

被引:171
|
作者
Zhang, Bo [1 ]
Studer, Armido [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
PROMOTED INTRAMOLECULAR CARBOAMINATION; CLICK-CHEMISTRY; OXIDATIVE DIAMINATION; MECHANISTIC PATHWAYS; ASYMMETRIC-SYNTHESIS; UNACTIVATED ALKENES; PALLADIUM; NITROGEN; AZIDES; AMINOOXYGENATION;
D O I
10.1021/ol500513b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed intermolecular aminoazidation of alkenes is described. This novel methodology provides an efficient approach to vicinal amino azides which can easily be transformed into other valuable amine derivatives. The commercially available N-fluorobenzenesulfonimide (NFSI) is used as a nitrogen-radical precursor and TMSN3 as the N-3 source. Yields are moderate to excellent, and for internal alkenes aminoazidation occurs with excellent diastereoselectivity.
引用
收藏
页码:1790 / 1793
页数:4
相关论文
共 50 条
  • [21] Copper-Catalyzed Oxyboration of Unactivated Alkenes
    Itoh, Taisuke
    Matsueda, Takumi
    Shimizu, Yohei
    Kanai, Motomu
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (45) : 15955 - 15959
  • [22] Copper-Catalyzed Enantioselective Arylalkynylation of Alkenes
    Wu, Yan
    He, Weimin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) : 2597 - 2599
  • [23] Copper-Catalyzed Regioselective Borylfluoromethylation of Alkenes
    Wu, Nuo-Yi
    Xu, Xiu-Hua
    Qing, Feng-Ling
    ACS CATALYSIS, 2019, 9 (06) : 5726 - 5731
  • [24] Copper-catalyzed oxytrifluoromethylation of unactivated alkenes
    Zhu, Rong
    Buchwald, Stephen L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [25] Copper-Catalyzed Oxidation of Alkenes and Heterocycles
    Leticia Garcia-Cabeza, Ana
    Javier Moreno-Dorado, F.
    Ortega, Maria J.
    Guerra, Francisco M.
    SYNTHESIS-STUTTGART, 2016, 48 (15): : 2323 - 2342
  • [26] COPPER-CATALYZED CYANOPROPYLATION OF ACTIVATED ALKENES
    Tang, Shi
    Li, Zhi-Hao
    Zhou, Dong
    Deng, You-Lin
    Ding, Guo-Liang
    Zhang, Qian
    Liu, Li-Ya
    Li, Shu-Hua
    SYNTHETIC COMMUNICATIONS, 2015, 45 (10) : 1231 - 1239
  • [27] Copper-catalyzed enantioselective arylalkynylation of alkenes
    Lei, Guangyue
    Zhang, Hanwen
    Chen, Bin
    Xu, Meichen
    Zhang, Guozhu
    CHEMICAL SCIENCE, 2020, 11 (06) : 1623 - 1628
  • [28] Copper-catalyzed methylative difunctionalization of alkenes
    Xu Bao
    Takayuki Yokoe
    Tu M. Ha
    Qian Wang
    Jieping Zhu
    Nature Communications, 9
  • [29] Copper-Catalyzed Enantioselective Hydroamination of Alkenes
    Liu, Richard Y.
    Buchwald, Stephen L.
    ORGANIC SYNTHESES, 2018, 95 : 80 - +
  • [30] Enantioselective Copper-Catalyzed Methylboration of Alkenes
    Chen, Bin
    Cao, Peng
    Liao, Yang
    Wang, Min
    Liao, Jian
    ORGANIC LETTERS, 2018, 20 (05) : 1346 - 1349