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 50 条
  • [21] REACTION OF AMINES WITH 1,3-DIENES CATALYZED BY NICKEL-COMPLEXES
    BAKER, R
    COOK, AH
    HALLIDAY, DE
    SMITH, TN
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (12): : 1511 - 1517
  • [22] Regioselective 1,4-Hydroamination of 1,3-Dienes by Photoredox/Cobalt Dual Catalysis
    Li, Pei-Ting
    Mou, Quansheng
    Yu, Wei
    ORGANIC LETTERS, 2025, 27 (08) : 1973 - 1978
  • [23] Theoretical study of Ni(0)-catalyzed intermolecular hydroamination of branched 1,3-dienes: reaction mechanism, regioselectivity, enantioselectivity, and prediction of the ligand
    Wang, Fen
    Chen, Changbao
    Zhang, Feng
    Meng, Qingxi
    JOURNAL OF MOLECULAR MODELING, 2025, 31 (01)
  • [24] Pd-catalyzed enantioselective intermolecular hydroamination of dienes with aliphatic amines
    Malcolmson, Steven
    Adamson, Nathan
    Hull, Ethan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [25] KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes
    Yunfei Xiang
    Ruisheng Du
    Shang Wang
    Xiang Wu
    Jie Tang
    Fan Yang
    Dong Xing
    Molecular Diversity, 2023, 27 : 1481 - 1487
  • [26] KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes
    Xiang, Yunfei
    Du, Ruisheng
    Wang, Shang
    Wu, Xiang
    Tang, Jie
    Yang, Fan
    Xing, Dong
    MOLECULAR DIVERSITY, 2023, 27 (03) : 1481 - 1487
  • [27] Fe(III)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes Improved by Using Triphenylphosphate as an Additive
    Kim, Ye Jin
    Kim, Dong Bin
    Youn, So Won
    ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (01)
  • [28] HYDROSILYLATION OF 1,3-DIENES BY PHENYLSILANE
    YUREV, VP
    SALIMGAREEVA, IM
    ZHEBAROV, OZ
    TOLSTIKOV, GA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (08): : 1772 - 1773
  • [29] TRIMETHYLSILYLCYCLOPENTADIENE REACTION WITH 1,3-DIENES
    YUREV, VP
    GAILYUNA.GA
    SULTANOV, AS
    KHVOSTEN.VI
    TOLSTIKO.GA
    ZHURNAL OBSHCHEI KHIMII, 1973, 43 (09): : 1986 - 1989
  • [30] Catalytic Enantioselective Intermolecular Three-Component Sulfenylative Difunctionalizations of 1,3-Dienes
    Liu, Xiao-Dong
    Ye, Ai -Hui
    Chen, Zhi-Min
    ACS CATALYSIS, 2023, 13 (04) : 2715 - 2722
12345