Selective Three-Component Reductive Alkylalkenylation of Unbiased Alkenes via Carbonyl-Directed Nickel Catalysis

被引：47
|
作者：
Wang, Fang [1 ]
Pan, Shiwei [1 ]
Zhu, Shengqing [1 ]
Chu, Lingling [1 ]
机构：
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Ctr Adv Low Dimens Mat, State Key Lab Modificat Chem Fibers & Polymer Mat, Shanghai 201620, Peoples R China
来源：
ACS CATALYSIS | 2022年 / 12卷 / 15期
基金：
中国国家自然科学基金;
关键词：
nickel catalysis; dicarbofunctionalization; alkenylation; unbiased alkenes; reductive coupling; CROSS-COUPLING REACTIONS; ASYMMETRIC HYDROVINYLATION; HALIDES; DICARBOFUNCTIONALIZATION; ALKENYLATION; OLEFINS; ESTERS; ACIDS; VINYL; 1,2-DIFUNCTIONALIZATION;
D O I：
10.1021/acscatal.2c02163
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A Ni-catalyzed enantioselective reductive three-component alkylalkenylation of beta,gamma-alkenyl ketones with cis-alkenyl iodides and fluoroalkyl iodides in the presence of Mn is reported. By leveraging five-membered nickellacycles stabilized by pendant ketone group and chiral bis(oxazoline) (BiOx) ligand, this three-component protocol allows efficient access to enantioenriched beta-alkenyl ketones from simple starting materials. Ni-catalyzed three-component alkylalkenylation of diverse electronically unbiased alkenes beyond beta,gamma-alkenyl ketones that enables regioselective construction of two C(sp(3))-C(sp(3)) and C(sp(3))-(sp(2)) bonds in one single operation is also demonstrated.
引用
收藏
页码：9779 / 9789
页数：11
相关论文
共 50 条
  • [1] General Method for Selective Three-Component Carboacylation of Alkenes via Visible-Light Dual Photoredox/Nickel Catalysis
    Wang, Zi-Kai
    Wang, Ya-Ping
    Rao, Zhi-Wu
    Liu, Chun-Yu
    Pan, Xian-Hua
    Guo, Lei
    ORGANIC LETTERS, 2023, 25 (10) : 1673 - 1677
  • [2] Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis
    Wang, Dingyi
    Ackermann, Lutz
    CHEMICAL SCIENCE, 2022, 13 (24) : 7256 - 7263
  • [3] Three-Component 1,2-Carboalkynylation of Alkenes Via Cooperative Nickel/Photoredox Catalysis
    Niu, Lujing
    Jin, Shengzhou
    Zhu, Meiqi
    Wang, Lanfen
    Wang, Dingyi
    ORGANIC LETTERS, 2025, 27 (13) : 3183 - 3187
  • [4] Enantioselective Directed Nickel-Catalyzed Three-Component Reductive Arylalkylation of Alkenes via the Carbometalation/Radical Cross-Coupling Sequence
    Dong, Zhan
    Xu, Changyu
    Chang, Jianchao
    Zhou, Sitian
    Sun, Peipei
    Li, Yuqiang
    Chen, Liang-An
    ACS CATALYSIS, 2024, 14 (07) : 4395 - 4406
  • [5] Three-Component Regioselective Aryl- and Alkenyl-Aminoalkylation of Alkenes via Cooperative Photoredox/Nickel Catalysis
    Ye, Fu
    Yuan, Weiming
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23): : 17708 - 17719
  • [6] Asymmetric Reductive Dicarbofunctionalization of Alkenes via Nickel Catalysis
    Anthony, David
    Diao, Tianning
    SYNLETT, 2020, 31 (15) : 1443 - 1447
  • [7] Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis
    Jiang, Heng
    Yu, Xiaoye
    Daniliuc, Constantin G.
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (26) : 14399 - 14404
  • [8] Three-Component Carboboration of Alkenes under Copper Catalysis
    Kageyuki, Ikuo
    Yoshida, Hiroto
    Takaki, Ken
    SYNTHESIS-STUTTGART, 2014, 46 (14): : 1924 - 1932
  • [9] Three-component enantioselective alkenylation of organophosphonates via nickel metallaphotoredox catalysis
    Li, Xiaofang
    Yuan, Mingbin
    Chen, Fan
    Huang, Zhonghou
    Qing, Feng-Ling
    Gutierrez, Osvaldo
    Chu, Lingling
    CHEM, 2023, 9 (01): : 154 - 169
  • [10] Nickel-Catalyzed Three-Component Reductive Alkylacylation of Electron-Deficient Activated Alkenes
    Wang, Lin
    Wang, Chuan
    ORGANIC LETTERS, 2020, 22 (22) : 8829 - 8835
12345