Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source

被引：38
|
作者：
Han, Jianlin
Li, Yufeng
Zhi, Sanjun
Pan, Yi
Timmons, Cody
Li, Guigen [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Peoples R China
[2] Nanjing Univ, State Key Lab Coordinat, Nanjing 210093, Peoples R China
[3] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 40期
关键词：
D O I：
10.1016/j.tetlet.2006.07.143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N,N-Dichloro-p-toluenesulfonamide (TsNCl2) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl2 to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient alpha,beta-unsaturated alkenes. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7225 / 7228
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Diamination of Unactivated Alkenes Using N-Fluorobenzenesulfonimide as Source of Electrophilic Nitrogen
    Sibbald, Paul A.
    Michael, Forrest E.
    ORGANIC LETTERS, 2009, 11 (05) : 1147 - 1149
  • [2] Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
    Wang, Liansheng
    Pan, Yi
    Hu, Hongwen
    HETEROCYCLIC COMMUNICATIONS, 2012, 18 (03) : 147 - 150
  • [3] Palladium-Catalyzed Aminocarbonylation of Aliphatic Alkenes with N,N-Dimethylformamide as an InSitu Source of CO
    Seidensticker, Thomas
    Furst, Marc R. L.
    Frauenlob, Robin
    Vondran, Johanna
    Paetzold, Eckhard
    Kragl, Udo
    Vorholt, Andreas J.
    CHEMCATCHEM, 2015, 7 (24) : 4085 - 4090
  • [4] Enantioselective palladium-catalyzed diamination of alkenes using N-fluorobenzenesulfonimide
    Ingalls, Erica L.
    Sibbald, Paul A.
    Kaminsky, Werner
    Michael, Forrest E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [5] Enantioselective Palladium-Catalyzed Diamination of Alkenes Using N-Fluorobenzenesulfonimide
    Ingalls, Erica L.
    Sibbald, Paul A.
    Kaminsky, Werner
    Michael, Forrest E.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (24) : 8854 - 8856
  • [6] Catalytic aminohalogenation reaction of β-nitrostyrenes with N,N-dichloro-p-toluenesulfonamide resulting in dichlorinated haloamides with opposite regiochemistry to previous systems
    Zhi, Sanjun
    Han, Jianlin
    Lin, Chen
    An, Guanghui
    Pan, Yi
    Li, Guigen
    SYNTHESIS-STUTTGART, 2008, (10): : 1570 - 1574
  • [7] Preparation of polymeric analogs of N,N-dichloro-p-toluenesulfonamide and their use for oxidation of alcohols, oxidative lactonization of diols, and chlorination of carbonyl compounds
    Kawasoe, S
    Kobayashi, K
    Ikeda, K
    Ito, T
    Kwon, TS
    Kondo, S
    Kunisada, H
    Yuki, Y
    JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 1997, A34 (08): : 1429 - 1438
  • [8] Palladium-Catalyzed N-Alkenylation of N-Aryl Phosphoramidates with Alkenes
    Li, Yu-An
    Wu, Ge
    Li, Jia
    MOLECULES, 2023, 28 (11):
  • [9] The application of NCTS (N-cyano-N-phenyl-p-toluenesulfonamide) in palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides
    Li, Jizhen
    Xu, Wenbin
    Ding, Junshuai
    Lee, Kuo-Hsiung
    TETRAHEDRON LETTERS, 2016, 57 (11) : 1205 - 1209
  • [10] Palladium-catalyzed cascade reactions of benzyl halides with N-allyl-N-(2-butenyl)-p-toluenesulfonamide
    Hu, YM
    Zhou, J
    Long, XT
    Han, JL
    Zhu, CJ
    Pan, Y
    TETRAHEDRON LETTERS, 2003, 44 (27) : 5009 - 5010
12345