Visible-Light-Induced Four-Component Ritter-Type Reaction: Access to β-Trifluoromethyl Imides

被引:6
|
作者
Ma, Ransong [1 ]
Ren, Yuanyuan [1 ]
Deng, Zhoubin [1 ]
Wang, Ke-Hu [1 ]
Wang, Junjiao [1 ]
Huang, Danfeng [1 ]
Lv, Xiaobo [3 ]
Hu, Yulai [1 ,2 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[3] Shanghai Sinofluoro Chem Co Ltd, Shanghai 201321, Peoples R China
基金
中国国家自然科学基金;
关键词
FUNCTIONALIZATION; ALKENES;
D O I
10.1021/acs.orglett.3c01291
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-induced four-component Ritter-type reactionwasdeveloped for the synthesis of beta-trifluoromethyl imides fromCF(3)Br, alkenes, carboxylic acids, and nitriles. This protocolfeatures mild reaction conditions, a broad substrate scope, and excellentfunctional group compatibility. Furthermore, this method has beenproven to be suitable for the late-stage diversification of drug molecules.A mechanism involving a Ritter-type reaction and Mumm rearrangementwas proposed on the basis of the control experiments.
引用
收藏
页码:4080 / 4085
页数:6
相关论文
共 50 条
  • [41] Visible-light-induced hydrogen evolution reaction with WSxSe2-x
    Gupta, Uttam
    Narang, Deepa S.
    BULLETIN OF MATERIALS SCIENCE, 2017, 40 (02) : 329 - 333
  • [42] Visible-Light-Induced Denitrification Oxygenation Reaction of α-Diazoesters to Construct α-Oxyimido Esters
    Liu Ruisheng
    Fu Shuangmin
    Chu Xiumin
    Zhang Lingli
    Ding Rou
    Zhao Xian'en
    Yue Huilan
    Wei Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (08) : 2462 - 2470
  • [43] Intramolecular Transamidation of Secondary Amides via Visible-Light-Induced Tandem Reaction
    Tang, Li
    Li, Xing-Meng
    Matuska, Jack H.
    He, Yan-Hong
    Guan, Zhi
    ORGANIC LETTERS, 2018, 20 (18) : 5618 - 5621
  • [44] Visible-Light-Induced Three-Component Reactions of α-Diazoesters, Indazoles, and Cyclic Ethers
    Wang, Wei
    Liu, Yan
    Yang, Qin
    Fu, Yang
    Ding, Qiuping
    Peng, Yiyuan
    SYNTHESIS-STUTTGART, 2024, 56 (24): : 3889 - 3902
  • [45] Visible-light-induced cascade reaction: a sustainable approach towards molecular complexity
    Ghosh, Sumit
    Pyne, Pranjal
    Ghosh, Anogh
    Choudhury, Swagata
    Hajra, Alakananda
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (08) : 1591 - 1628
  • [46] Visible-Light-Induced Enantioselective Chemodivergent Three-Component Radical Tandem Reactions
    Liu Ping
    Sun Peipei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (10) : 3661 - 3663
  • [47] Visible-Light-Induced Domino Perfluoroalkylation/Cyclization to Access Perfluoroalkylated Quinazolinones by an EDA Complex
    Meng, Fei
    Cui, Yangyang
    Xu, Wen
    Yang, Wen-Chao
    ORGANIC LETTERS, 2024, 26 (32) : 6884 - 6888
  • [48] Four-Component Reaction Access to Nitrile-Substituted All-Carbon Quaternary Centers
    Hu, Xin
    Bian, Qiang
    Wang, Zheng-Lin
    Guo, Lin-Jie
    Wang, Yi-Ze Xu Ge
    Xu, Da-Zhen
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 66 - 75
  • [49] Visible-Light-Induced Regioselective Cascade Radical Cyclization of α-Bromocarbonyls: Access to Benzazepine Derivatives
    Zhou, Nengneng
    Zhao, Fangli
    Wang, Lei
    Gao, Xiang
    Zhao, Xiaowei
    Zhang, Man
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (04): : 2238 - 2246
  • [50] Visible-Light-Induced Three-Component Radical Strategy for the Synthesis of β-Amino Alcohols
    Wu, Zhongtian
    Su, Kai
    Liu, Huiying
    Wang, Ze
    Wang, Zhaoshan
    Duan, Xiu
    Chen, Dong
    Feng, Jie
    Wu, Xinxin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,