Copper Promoted Regio- and Stereoselective Aminochlorination of Alkynes and Alkenes with NFSI

被引:24
|
作者
Wang, Weilin [1 ,2 ]
Liu, Lingyan [1 ,2 ]
Chang, Weixing [1 ,2 ]
Li, Jing [1 ,2 ,3 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Weijin Rd 94, Tianjin 300071, Peoples R China
关键词
alkenes; alkynes; aminochlorination; chloroenamine; NFSI; NITROGEN-CENTERED RADICALS; ELECTROPHILIC DIAMINATION; AMINOHALOGENATION REACTION; CINNAMIC ESTERS; BROMINE SOURCES; HALOGEN SOURCES; OLEFINS; AMINOBROMINATION; TRIFLUOROMETHYLATION; COMPLEX;
D O I
10.1002/chem.201801262
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and rapid copper-promoted aminochlorination of unactivated alkynes and alkenes with N-fluorobenzenesulfonimide (NFSI) was developed. Two series of chloroenamines and chloroamines were obtained in good to high yields. The chlorinated enamines could be obtained in a single Econfiguration. This reaction involved a radical process and the CuCl2 acted as the Cl source and NFSI as the N source.
引用
收藏
页码:8542 / 8547
页数:6
相关论文
共 50 条
  • [1] Copper-catalyzed regio- and stereoselective fluorocarboalkynylation of alkynes
    Zhao, Binlin
    Zheng, Yukun
    Zhu, Tianxiang
    Wang, Mengning
    Wang, Minyan
    Ma, Mengtao
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24): : 6857 - 6862
  • [2] Regio- and Stereoselective Carbobismuthination of Alkynes
    Nishimoto, Yoshihiro
    Takeuchi, Midori
    Yasuda, Makoto
    Baba, Akio
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 1051 - 1054
  • [3] Regio- and Stereoselective Chlorocyanation of Alkynes
    Barrado, Alejandro G.
    Zielinski, Adam
    Goddard, Richard
    Alcarazo, Manuel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13401 - 13405
  • [4] Regio- and Stereoselective Iodoacyloxylations of Alkynes
    Priebbenow, Daniel L.
    Gable, Robert W.
    Baell, Jonathan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4412 - 4418
  • [5] Chemo-, regio-, and stereoselective iron- catalysed hydroboration of alkenes and alkynes
    Greenhalgh, Mark D.
    Thomas, Stephen P.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (95) : 11230 - 11232
  • [6] Recent Advances in Cobalt-Catalyzed Regio- or Stereoselective Hydrofunctionalization of Alkenes and Alkynes
    Li, Yan
    Lu, Xi
    Fu, Yao
    [J]. CCS CHEMISTRY, 2024, 6 (05): : 1130 - 1156
  • [7] Cobalt- and Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling of Alkynes, Allenes, and Alkenes with Alkenes
    Jeganmohan, Masilamani
    Cheng, Chien-Hong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) : 10876 - 10886
  • [8] Ionic liquid promoted regio- and stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction
    Ranu, Brindaban C.
    Chattopadhyay, Kalicharan
    Ghosh, Sudip
    Jana, Ranjan
    [J]. JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2008, 85 (12) : 1199 - 1204
  • [9] Regio- and stereoselective hydrosilylation of immobilized terminal alkynes
    Pedersen, Palle J.
    Henriksen, Jonas
    Gotfredsen, Charlotte H.
    Clausen, Mads H.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (43) : 6220 - 6223
  • [10] Regio- and Stereoselective Reductive Coupling of Alkynes and Crotononitrile
    Cui, Kun
    Li, Yan-Lin
    Li, Gongqiang
    Xia, Ji-Bao
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (50) : 23001 - 23009