Radical Alkylation of Imines with 4-Alkyl-1,4-dihydropyridines Enabled by Photoredox/Bronsted Acid Cocatalysis

被引:85
|
作者
Zhang, Hong-Hao [1 ]
Yu, Shouyun [1 ]
机构
[1] Nanjing Univ, State Key Lab Analyt Chem Life Sci, Jiangsu Key Lab Adv Organ Mat, Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 19期
基金
中国国家自然科学基金;
关键词
COUPLED ELECTRON-TRANSFER; CARBON-CARBON BOND; VISIBLE-LIGHT; HANTZSCH ESTER; TRANSFER HYDROGENATION; SYNTHETIC APPLICATIONS; ASYMMETRIC ALKYLATION; CATALYSIS; CHEMISTRY; ALDEHYDES;
D O I
10.1021/acs.joc.7b01425
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radical alkylation of imines with 4-alkyl-1,4-dihydropyridines cocatalyzed by iridium/ruthenium complex and Bronsted acid under visible light irradiation has been achieved. Both aldimines and ketithines can undergo this transformation. Common functional groups, such as hydroxyl groups, ester, amide, ether, cyanide, and heterocycles, can be tolerated in this reaction. A variety of structurally diverse amines (57 examples) have been produced with up to 98% isolated yields using this method.
引用
收藏
页码:9995 / 10006
页数:12
相关论文
共 50 条
  • [31] Electrochemical-induced radical allylation via the fragmentation of alkyl 1,4-dihydropyridines
    Chen, Xiaoping
    Luo, Xiaosheng
    Wang, Ping
    TETRAHEDRON LETTERS, 2022, 91
  • [32] UNUSUAL OXIDATIVE DEALKYLATION OF CERTAIN 4-ALKYL-1,4-DIHYDROPYRIDINES WITH MNO2/BENTONITE USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT(II)
    DELGADO, F
    ALVAREZ, C
    GARCIA, O
    PENIERES, G
    MARQUEZ, C
    SYNTHETIC COMMUNICATIONS, 1991, 21 (21) : 2137 - 2141
  • [33] Late-Stage Alkylation of N-Containing Heteroarenes Enabled by Homolysis of Alkyl-1,4-dihydropyridines under Blue LED Irradiation
    Chen, Xiaoping
    Luo, Xiaosheng
    Wang, Kaiqian
    Liang, Feng
    Wang, Ping
    SYNLETT, 2020,
  • [34] Late-Stage Alkylation of N-Containing Heteroarenes Enabled by Homolysis of Alkyl-1,4-dihydropyridines under Blue LED Irradiation
    Chen, Xiaoping
    Luo, Xiaosheng
    Wang, Kaiqian
    Liang, Feng
    Wang, Ping
    SYNLETT, 2021, 32 (07) : 733 - 737
  • [35] Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2 as an oxidant (vol 22, pg 5599, 2020)
    Dong, Jianyang
    Yue, Fuyang
    Xu, Wentao
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    GREEN CHEMISTRY, 2022, 24 (16) : 6319 - 6319
  • [36] Synthesis of Indenones via Persulfate Promoted Radical Alkylation/Cyclization of Biaryl Ynones with 1,4-Dihydropyridines
    Wang, Wanwan
    Yu, Lei
    MOLECULES, 2024, 29 (02):
  • [37] Radical C4-H Arylation of 1,4-Dihydropyridines with Cyanoarenes
    Guo, Huaixuan
    Qiu, Shiqin
    Xu, Peng
    HELVETICA CHIMICA ACTA, 2024, 107 (12)
  • [38] Visible-Light-Mediated Aromatic Substitution Reactions of Cyanoarenes with 4-Alkyl-1,4-dihydropyridines through Double Carbon-Carbon Bond Cleavage
    Nakajima, Kazunari
    Nojima, Sunao
    Sakata, Ken
    Nishibayashi, Yoshiaki
    CHEMCATCHEM, 2016, 8 (06) : 1028 - 1032
  • [39] Radical Addition of 4-Hydroxyquinazolines and Alkylation of Quinones by the Electro-Induced Homolysis of 4-Alkyl-1,4-di-hydropyridines
    Luo, Xiaosheng
    Feng, Qiping
    Wang, Ping
    SYNTHESIS-STUTTGART, 2022, 54 (11): : 2696 - 2706
  • [40] Visible-Light-Promoted Cross-Coupling Reactions of 4-Alkyl-1,4-dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides
    Li, Jian
    Yang, Xin-Er
    Wang, Shan-Le
    Zhang, Long-Long
    Zhou, Xiao-Zhou
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC LETTERS, 2020, 22 (12) : 4908 - 4913