Visible-light-mediated difluoromethylphosphonation of alkenes for the synthesis of CF2P-containing heterocycles

被引：8
|
作者：
Yang, Qiang [1 ]
Lin, Qing-Qing [1 ]
Xing, Hou-Ying [1 ]
Zhao, Zhi-Gang [1 ]
机构：
[1] Southwest Minzu Univ, Coll Chem & Environm Protect Engn, Chengdu 610041, Sichuan, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 24期
关键词：
COPPER-CATALYZED OXYTRIFLUOROMETHYLATION; DIASTEREOSELECTIVE SYNTHESIS; FLUOROALKYLATION REACTIONS; PHOTOREDOX CATALYSIS; TRIFLUOROMETHYLATION; DIFLUOROALKYLATION; INHIBITORS; CYCLIZATION; DRIVEN; ARYL;
D O I：
10.1039/c9qo01030k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Difluoromethylphosphonate, as an in vivo stable phosphate bio-isostere, is an important organofluorophosphine block. In this paper, an efficient and general protocol for the construction of CF2P-containing heterocycles via visible-light-mediated nucleophilic cyclization of unsaturated carboxylic acids, alcohol and sulfonamides has been developed. This reaction can be carried out smoothly under mild conditions with less catalyst loading, producing several types of CF2P-containing heterocycles, including CF2P-lactone, CF2P-phthalide, CF2P-tetrahydrofuran and CF2P-pyrrolidine.
引用
收藏
页码：3939 / 3943
页数：5
相关论文
共 50 条
  • [21] Visible-light-mediated multicomponent reaction for secondary amine synthesis
    Wang, Xiaochen
    Zhu, Binbing
    Dong, Jianyang
    Tian, Hao
    Liu, Yuxiu
    Song, Hongjian
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2021, 57 (41) : 5028 - 5031
  • [22] Intramolecular, Visible-Light-Mediated Aza Paterno-Buchi Reactions of Unactivated Alkenes
    Blackmun, Dominique E.
    Chamness, Stephen A. .
    Schindler, Corinna S.
    ORGANIC LETTERS, 2022, 24 (16) : 3053 - 3057
  • [23] Visible-Light-Mediated Amide Synthesis in Deep Eutectic Solvents
    Procopio, Debora
    Marset, Xavier
    Guillena, Gabriela
    Di Gioia, Maria Luisa
    Ramon, Diego J.
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 870 - 876
  • [24] Synthesis of Selenaheterocycles via Visible-Light-Mediated Radical Cyclization
    Aganda, Kim Christopher C.
    Lee, Anna
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (22) : 5149 - 5154
  • [25] Visible-Light-Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides
    Zurro, Mercedes
    Torres-Oya, Sergio
    Merino, Estibaliz
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [26] Visible-Light-Mediated [2+2] Photocycloadditions of Alkynes
    Zhang, Qing-Bao
    Li, Feng
    Pan, Bin
    Yu, Lei
    Yue, Xiang-Guo
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (43)
  • [27] Visible-Light-Mediated TiO2-Catalyzed Aerobic Dehydrogenation of N-Heterocycles in Batch and Flow
    Noh, Junghoon
    Cho, Jun-Young
    Park, Mincheol
    Park, Boyoung Y.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 10682 - 10692
  • [28] Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
    Wang, Leifeng
    Wu, Fengjin
    Chen, Jiean
    Nicewicz, David A.
    Huang, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) : 6896 - 6900
  • [29] Visible-light-mediated radical aryltrichloromethylation of N-arylacrylamides for the synthesis of trichloromethyl-containing oxindoles
    Zhu, Mei
    Fu, Weijun
    HETEROCYCLIC COMMUNICATIONS, 2015, 21 (06) : 387 - 390
  • [30] Visible-Light-Mediated NHC and Tertiary Amine Catalysis Enabling a-H Acylation of Alkenes
    Li, Shihao
    Wang, Sheng
    Feng, Huiyi
    Tang, Fei
    Yang, Wenqing
    Li, Xiao-Xuan
    Zhang, Qi
    Fan, Shilu
    Feng, Yi-Si
    ORGANIC LETTERS, 2023, 25 (19) : 3369 - 3374
12345