Copper-Catalyzed Intermolecular Hydroamination of Internal Alkynes with Anilines and Amines

被引：24
作者：
Ishikawa, Tomoki [1 ]
Sonehara, Taro [1 ]
Minakawa, Maki [1 ]
Kawatsura, Motoi [1 ]
机构：
[1] Nihon Univ, Coll Humanities & Sci, Dept Chem, Setagaya Ku, Tokyo 1568550, Japan
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 06期
关键词：
H BOND ACTIVATION; ANTI-MARKOVNIKOV ADDITION; TERMINAL ALKYNES; TRIFLUOROMETHYL GROUP; SECONDARY-AMINES; REGIOSELECTIVE SYNTHESIS; COPPER(I)-CATALYZED HYDROAMINATION; MEDICINAL CHEMISTRY; ALLYLIC AMINATION; BUILDING-BLOCKS;
D O I：
10.1021/acs.orglett.6b00352
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper-catalyzed regioselective intermolecular hydroamination of the aryl and trifluoromethyl group or electron-withdrawing group substituted internal alkynes with amines has been accomplished. The reaction was effectively catalyzed by the ligand-free Cu(OTf)(2) and afforded the intended amine derivatives in good yields after treatment of NaBH3CN.
引用
收藏
页码：1422 / 1425
页数：4
相关论文
共 99 条
  • [1] TiCl4-catalyzed intermolecular hydroamination reactions
    Ackermann, L
    [J]. ORGANOMETALLICS, 2003, 22 (22) : 4367 - 4368
  • [2] General zinc-catalyzed intermolecular hydroamination of terminal alkynes
    Alex, Karolin
    Tillack, Annegret
    Schwarz, Nicolle
    Beller, Matthias
    [J]. CHEMSUSCHEM, 2008, 1 (04) : 333 - 338
  • [3] Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles
    Alex, Karolin
    Tillack, Annegret
    Schwarz, Nicolle
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2304 - 2307
  • [4] Catalytic hydroamination of alkynes and norbornene with neutral and cationic tantalum imido complexes
    Anderson, LL
    Arnold, J
    Bergman, RG
    [J]. ORGANIC LETTERS, 2004, 6 (15) : 2519 - 2522
  • [5] Hydroamination of terminal alkynes with secondary amines catalyzed by copper: regioselective access to amines
    Bahri, Janet
    Blieck, Remi
    Jamoussi, Bassem
    Taillefer, Marc
    Monnier, Florian
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (56) : 11210 - 11212
  • [6] Copper-Catalyzed Hydroamination of Alkynes with Aliphatic Amines: Regioselective Access to (1E,3E)-1,4-Disubstituted-1,3-dienes
    Bahri, Janet
    Jamoussi, Bassem
    van der Lee, Arie
    Taillefer, Marc
    Monnier, Florian
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1224 - 1227
  • [7] VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE
    BARANGER, AM
    WALSH, PJ
    BERGMAN, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 2753 - 2763
  • [8] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
    Begue, Jean-Pierre
    Bonnet-Delpon, Daniele
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 992 - 1012
  • [9] Bemoud E., 2015, CATAL SCI TECHNOL, V5, P2017
  • [10] An (Aminopyrimidinato)titanium Catalyst for the Hydroamination of Alkynes and Alkenes
    Brahms, Christian
    Tholen, Patrik
    Saak, Wolfgang
    Doye, Sven
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (33) : 7583 - 7592
12345678910