Copper-Catalyzed Hydroamination of Terminal Allenes

被引:53
|
作者
Blieck, Remi [1 ]
Bahri, Janet [1 ]
Taillefer, Marc [1 ]
Monnier, Florian [1 ]
机构
[1] Ecole Natl Super Chim Montpellier, Inst Charles Gerhardt Montpellier, UMR 5253, CNRS,AM2N, 8 Rue Ecole Normale, F-34296 Montpellier 5, France
关键词
INTERMOLECULAR HYDROAMINATION; INTRAMOLECULAR HYDROAMINATION; REGIOSELECTIVE ACCESS; ALLYLIC AMINES; ARYLATION; ALKENES; ALKYNES; COMPLEXES; ZIRCONIUM; EFFICIENT;
D O I
10.1021/acs.orglett.6b00452
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ligand-free copper-catalyzed hydroamination of allenes has been accomplished in the presence of cyclic secondary amines or anilines derivatives. This novel methodology undergoes the selective generation of (E)-allylamines under smooth conditions with total regio- and stereoselectivity.
引用
收藏
页码:1482 / 1485
页数:4
相关论文
共 50 条
  • [1] The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes
    Kim, Hong Ki
    Mane, Manoj, V
    Montgomery, John
    Baik, Mu-Hyun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (40) : 9456 - 9463
  • [2] Copper-Catalyzed hydroamination of alkynes and allenes. Scope and mechanism studies
    Monnier, Florian
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [3] Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Development
    Perego, Luca Alessandro
    Blieck, Remi
    Groue, Antoine
    Monnier, Florian
    Taillefer, Marc
    Ciofini, Ilaria
    Grimaud, Laurence
    [J]. ACS CATALYSIS, 2017, 7 (07): : 4253 - 4264
  • [4] Copper-catalyzed hydroamination of propargyl imidates
    Fricke, Patrick
    Fennie, Michael
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [5] Copper-Catalyzed Enantioselective Hydroamination of Alkenes
    Liu, Richard Y.
    Buchwald, Stephen L.
    [J]. ORGANIC SYNTHESES, 2018, 95 : 80 - +
  • [6] Copper-catalyzed hydroamination of propargyl imidates
    Fricke, Patrick J.
    Stasko, Jenna L.
    Robbins, Dylan T.
    Gardner, Alexander C.
    Stash, Jacqueline
    Ferraro, Mark J.
    Fennie, Michael W.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (48) : 4510 - 4513
  • [7] Copper-catalyzed intermolecular hydroamination of alkenes
    Taylor, Jason G.
    Whittall, Neil
    Hii, King Kuok
    [J]. ORGANIC LETTERS, 2006, 8 (16) : 3561 - 3564
  • [8] Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes
    Zhao, Wanxiang
    Montgomery, John
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) : 9763 - 9766
  • [9] Enantioselective Copper-Catalyzed Hydroamination of Vinylarenes with Anthranils
    Xie, Fang
    Shen, Bingxue
    Li, Xingwei
    [J]. ORGANIC LETTERS, 2018, 20 (22) : 7154 - 7157
  • [10] Recent Progress in the Copper-Catalyzed Cascade Cyclization Involving Intramolecular Hydroamination of Terminal Alkynes
    Tan, Tong-De
    Chen, Yang-Bo
    Fan, Xin-Yang
    Ye, Long-Wu
    [J]. SYNLETT, 2019, 30 (18) : 2035 - 2040