Photoredox-Catalyzed Markovnikov Hydroamination of Alkenes with Azoles

被引:0
|
作者
Nie, Jinhuan [1 ]
Shi, Yutao [1 ]
Gan, Mengran [1 ]
Huang, Huawen [1 ,2 ]
Ji, Xiaochen [1 ,2 ]
机构
[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environmentally Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
关键词
D O I
10.1021/acs.orglett.4c03418
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light induced intermolecular hydroamination of alkenes with azoles is reported, delivering pharmaceutically valuable N-benzyl azoles in high yields with excellent Markovnikov selectivity. Mechanistic studies suggest that the process is initiated by the energy transfer of the excited photocatalyst with alkenes, followed by the single electron reduction, protonation, and subsequent single electron oxidation to afford the key alkyl carbocation intermediate. This protocol exhibits advantages of broad functional group tolerance, excellent atom economy, high efficiency, and mild reaction conditions.
引用
收藏
页码:9481 / 9485
页数:5
相关论文
共 50 条
  • [1] Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System
    Nguyen, Tien M.
    Nicewicz, David A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (26) : 9588 - 9591
  • [2] Photoredox-Catalyzed Hydrocarboxymethylation of Alkenes
    Fang, Jie
    Hu, Qiang
    Dong, Wan-Li
    Xu, Guo-Qiang
    Hu, Xiu-Qin
    Luo, Yong-Chun
    Xu, Peng-Fei
    CCS CHEMISTRY, 2021, 3 (10): : 95 - 104
  • [3] Photoredox and Cobalt-Catalyzed Markovnikov-Selective Radical Hydroamination of Unactivated Alkenes with Anilines
    Miao, Huanran
    Dong, Honglin
    Meng, Qi
    Feng, Cong
    Chen, Yukun
    Zhang, Ge
    Zhang, Qian
    ORGANIC LETTERS, 2025, 27 (13) : 3296 - 3301
  • [4] Photoredox-Catalyzed Difunctionalization of Alkenes with Sulfilimines
    Yu, Tingwei
    Jin, Zhe
    Ji, Yan
    Yang, Aihong
    Jia, Penghao
    ORGANIC LETTERS, 2024, 26 (37) : 7944 - 7948
  • [5] Organic Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles
    Wang, Ban
    Mccabe, Gavin E.
    Parrish, Mitchell J.
    Singh, Jujhar
    Zeller, Matthias
    Deng, Yongming
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1179 - 1184
  • [6] Photoredox-catalyzed difunctionalization of alkenes with quinoxalinone and chloroform
    Jiang, Xinye
    Shen, Jiabin
    Ye, Zhiping
    Shen, Chao
    MOLECULAR CATALYSIS, 2024, 569
  • [7] Recent Advances in Photoredox-Catalyzed Difunctionalization of Alkenes
    Liu, Yong
    Liu, Huan
    Liu, Xiao
    Chen, Zhangpei
    CATALYSTS, 2023, 13 (07)
  • [8] Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes
    Zhang, Zuxiao
    Tang, Xiaojun
    Thomoson, Charles S.
    Dolbier, William R., Jr.
    ORGANIC LETTERS, 2015, 17 (14) : 3528 - 3531
  • [9] Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams
    Giraldi, Valentina
    Magagnano, Giandomenico
    Giacomini, Daria
    Cozzi, Pier Giorgio
    Gualandi, Andrea
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 2461 - 2468
  • [10] Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes
    Du, Xiaoyong
    Cheng-Sanchez, Ivan
    Nevado, Cristina
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (23) : 12532 - 12540