Synthesis of trifluoromethylthioesters from aldehydes via a visible light-promoted radical process

被引:18
|
作者
Wang, Meng-Yue [1 ]
Zhu, Xue-Qing [1 ]
Zhang, Xing-Long [1 ]
Guo, Rui-Li [1 ]
Jia, Qiong [1 ]
Wang, Yong-Qiang [1 ]
机构
[1] Northwest Univ, Coll Chem & Mat Sci, Sch Foreign Languages, Key Lab Synthet & Nat Funct Mol Chem,Minist Educ, Xian 710069, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINE; TRIPHENYLPHOSPHINE; CATALYSIS; ESTERS;
D O I
10.1039/d0ob01160f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein an efficient, economical, and scalable trifluoromethylthiolation of aldehydes to generate trifluoromethylthioestersviaa visible light-promoted radical process. The transformation features cheap reagents, simple operation, a broad substrate scope, and especially no metal involved in the reaction. Trifluoromethylthiolations of several complex aldehyde-containing bioactive compounds have been realized; thus the approach has the potential to be an important tool for the late-stage functionalization of advanced synthetic intermediates and bioactive molecules, and should have many applications in medicinal chemistry.
引用
收藏
页码:5918 / 5926
页数:9
相关论文
共 50 条
  • [1] Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process
    Ye, Zhegao
    Lei, Ziran
    Ye, Xiaodong
    Zhou, Liejin
    Wang, Yanan
    Yuan, Zheliang
    Gao, Feng
    Britton, Robert
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 765 - 775
  • [2] Designing radical chemistry by visible light-promoted homolysis
    Protti, Stefano
    Ravelli, Davide
    Fagnoni, Maurizio
    TRENDS IN CHEMISTRY, 2022, 4 (04): : 305 - 317
  • [3] Synthesis of arylacylated oxindoles via visible light-promoted Smiles rearrangement
    Liu, Yihuo
    Ding, Siyu
    Xu, Mingli
    Xu, Jinli
    Cheng, Dongping
    Wang, Hong
    Xu, Xiaoliang
    CHEMISTRYSELECT, 2022, 7 (34):
  • [4] Visible Light-Promoted Radical Reactions of Diazo Compounds
    Li Sen
    Zhou Lei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 3944 - 3958
  • [5] Synthesis of ortho-(Fluoro)alkylated Pyridines via Visible Light-Promoted Radical Isocyanide Insertion
    Tong, Kun
    Zheng, Tianyi
    Zhang, Yan
    Yu, Shouyun
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3681 - 3686
  • [6] Metal-Free, Visible Light-Promoted Aerobic Aldehydes Oxidation
    Hamami, Zine Eddine
    Vanoye, Laurent
    Fongarland, Pascal
    de Bellefon, Claude
    Favre-Reguillon, Alain
    JOURNAL OF FLOW CHEMISTRY, 2016, 6 (03) : 206 - 210
  • [7] Metal-Free, Visible Light-Promoted Aerobic Aldehydes Oxidation
    Zine Eddine Hamami
    Laurent Vanoye
    Pascal Fongarland
    Claude de Bellefon
    Alain Favre-Reguillon
    Journal of Flow Chemistry, 2016, 6 : 206 - 210
  • [8] Visible light-promoted selenocyclofunctionalization
    Conner, Elizabeth
    Crocker, Katherine
    Ragains, Justin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [9] Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts
    Jiang, Heng
    Cheng, Yuanzheng
    Wang, Ruzhi
    Zhang, Yan
    Yu, Shouyun
    CHEMICAL COMMUNICATIONS, 2014, 50 (46) : 6164 - 6167
  • [10] Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides
    Lu, Juan
    Li, Lei
    He, Xiang-Kui
    Xu, Guo-Yong
    Xuan, Jun
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (06) : 1646 - 1650