NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant

被引：22
|
作者：
Yao, Wei-Wei [1 ,2 ]
Li, Ran [1 ,2 ]
Li, Jiang-Fei [1 ,2 ]
Sun, Juan [3 ]
Ye, Mengchun [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elernentoorgan Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Coll Chem, Key Lab Adv Energy Mat Chem, Dept Chem, Tianjin 300071, Peoples R China
来源：
GREEN CHEMISTRY | 2019年 / 21卷 / 09期
基金：
中国国家自然科学基金;
关键词：
BOND-FORMING HYDROGENATION; ASYMMETRIC TRANSFER HYDROGENATION; NICKEL CATALYSIS; ALLYLIC ALCOHOLS; 2+2+2 CYCLOADDITION; CONJUGATED ALKYNES; AZA-NICKELACYCLE; ALDEHYDES; CARBONYL; AMINES;
D O I：
10.1039/c9gc00653b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.
引用
收藏
页码：2240 / 2244
页数：5
相关论文
共 50 条
  • [21] Rhodium-Catalyzed Reductive Cleavage of Aryl Carbamates Using Isopropanol as a Reductant
    Yasui, Kosuke
    Higashino, Masaya
    Chatani, Naoto
    Tobisu, Mamoru
    SYNLETT, 2017, 28 (19) : 2569 - 2572
  • [22] Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes
    Pan, Qi
    Ping, Yuanyuan
    Wang, Yifan
    Guo, Ya
    Kong, Wangqing
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (27) : 10282 - 10291
  • [23] Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes
    Li, Xiaofang
    Chu, Lingling
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (10) : 4101 - 4102
  • [24] Visible-Light-Antenna Ligand-Enabled Samarium-Catalyzed Reductive Transformations
    Kuribara, Takahito
    Kaneki, Ayahito
    Matsuda, Yu
    Nemoto, Tetsuhiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (30) : 20904 - 20912
  • [25] Intramolecular Ni-catalyzed reductive coupling enables enantiodivergent synthesis of linoxepin
    Liu, Zi-Hao
    Xiao, Jian
    Zhai, Qian-Qian
    Tang, Xi
    Xu, Li-Jun
    Zhuang, Zhi-Yuan
    Wang, Ya-Wen
    Peng, Yu
    CHEMICAL COMMUNICATIONS, 2024, 60 (06) : 694 - 697
  • [26] Development of Ni-catalyzed enantioselective reductive cross-coupling reactions
    Reisman, Sarah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [27] Theoretical studies on Rh- and Ni-catalyzed reductive coupling reactions
    Liu, Peng
    Houk, Kendall N.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [28] Ni-Catalyzed Reductive Coupling of Heteroaryl Bromides with Tertiary Alkyl Halides
    Lin, Quan
    Gong, Hegui
    Wu, Fan
    ORGANIC LETTERS, 2022, 24 (49) : 8996 - 9000
  • [29] Ni-catalyzed, enantioselective three-component radical relayed reductive coupling of alkynes: Synthesis of axially chiral styrenes
    Li, Quan-Zhe
    Li, Zi-Hao
    Kang, Jun-Chen
    Ding, Tong-Mei
    Zhang, Shu-Yu
    CHEM CATALYSIS, 2022, 2 (11): : 3185 - 3195
  • [30] Stereoselective synthesis of pentasubstituted 1,3-dienes via Ni-catalyzed reductive coupling of unsymmetrical internal alkynes
    Zhou, Zhijun
    Chen, Jiachang
    Chen, Herong
    Kong, Wangqing
    CHEMICAL SCIENCE, 2020, 11 (37) : 10204 - 10211
12345