Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines

被引：84
作者：
Yang, Xiao-Hui [1 ]
Lu, Alexander [1 ]
Dong, Vy M. [1 ]
机构：
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 40期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
ANTI-MARKOVNIKOV HYDROAMINATION; PALLADIUM-CATALYZED HYDROAMINATION; INTRAMOLECULAR HYDROAMINATION/CYCLIZATION; UNACTIVATED ALKENES; ALKYL AMINES; COMPLEXES; VINYLARENES; DIENES; ADDITIONS; OLEFINS;
D O I：
10.1021/jacs.7b09188
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Bronsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.
引用
收藏
页码：14049 / 14052
页数：4
相关论文
共 60 条
  • [1] Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
    Adamson, Nathan J.
    Hull, Ethan
    Malcolmson, Steven J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) : 7180 - 7183
  • [2] Ananikov V.P., 2014, Topics in Organometallic Chemistry, V343
  • [3] [Anonymous], 1870, LIEBIGS ANN CHEM
  • [4] PALLADIUM-CATALYZED ADDITIONS OF AMINES TO CONJUGATED DIENES - ALTERATION OF BEHAVIOR OF (TRIPHENYLPHOSPHINE)PALLADIUM CATALYSTS WITH AMINE HYDROIODIDE SALTS
    ARMBRUSTER, RW
    MORGAN, MM
    SCHMIDT, JL
    LAU, CM
    RILEY, RM
    ZABROWSKI, DL
    DIECK, HA
    [J]. ORGANOMETALLICS, 1986, 5 (02) : 234 - 237
  • [5] Palladium-catalysed regioselective hydroamination of 1,3-dienes: synthesis of allylic amines
    Banerjee, Debasis
    Junge, Kathrin
    Beller, Matthias
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (04): : 368 - 372
  • [6] A General Catalytic Hydroamidation of 1,3-Dienes: Atom-Efficient Synthesis of N-Allyl Heterocycles, Amides, and Sulfonamides
    Banerjee, Debasis
    Junge, Kathrin
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) : 1630 - 1635
  • [7] Beller M, 1999, CHEM-EUR J, V5, P1306, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1306::AID-CHEM1306>3.0.CO
  • [8] 2-4
  • [9] Brinkmann C., 2012, J AM CHEM SOC, V134, P2193
  • [10] Bronner SM, 2014, CHEM SCI, V5, P101, DOI [10.1039/c3sc51897c, 10.1039/C3SC51897C]
123456