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
  • [31] Visible-light-mediated oxidation of hydroxylamines: A new pathway to indole synthesis
    Baldwin, Leslie
    Zheng, Nan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [32] Metal-Free Visible-Light-Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow
    Barthelemy, Anne-Laure
    Dagousset, Guillaume
    Magnier, Emmanuel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1429 - 1432
  • [33] Visible-Light-Mediated Synthesis of α-Halomethyl Ketones from Terminal Alkynes
    Shah, Iftkhar Hussain
    Kumar, Sourav
    Kumar, Jaswant
    Raheem, Shabnam
    Rizvi, Masood Ahmad
    Shah, Bhahwal Ali
    CHEMPHOTOCHEM, 2022, 6 (03)
  • [34] Visible-light-mediated tandem phosphorylation/cyclization for the synthesis of phosphorylated oxindoles
    Mao, Liu-Liang
    Zhou, An-Xi
    Zhu, Xian-Hong
    Quan, Li-Xia
    Chen, Fayun
    Wan, Jie-Ping
    Lai, Yin-Long
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (06) : 1196 - 1199
  • [35] Sustainable Strategy Utilizing Biomass: Visible-Light-Mediated Synthesis of -Valerolactone
    Verma, Sanny
    Baig, R. B. Nasir
    Nadagouda, Mallikarjuna N.
    Varma, Rajender S.
    CHEMCATCHEM, 2016, 8 (04) : 690 - 693
  • [36] Visible-Light-Mediated Metal-Free Synthesis of Trifluoromethylselenolated Arenes
    Ghiazza, Clement
    Debrauwer, Vincent
    Monnereau, Cyrille
    Khrouz, Lhoussain
    Medebielle, Maurice
    Billard, Thierry
    Tlili, Anis
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) : 11781 - 11785
  • [37] Norcaradiene Synthesis via Visible-Light-Mediated Cyclopropanation Reactions of Arenes
    Guo, Yujing
    Thanh Vinh Nguyen
    Koenigs, Rene M.
    ORGANIC LETTERS, 2019, 21 (21) : 8814 - 8818
  • [38] Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones
    Bui, Tien Tan
    Tran, Van Hieu
    Kim, Hee-Kwon
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 341 - 347
  • [39] External-Photocatalyst-Free Visible-Light-Mediated Synthesis of Indolizines
    Sahoo, Basudev
    Hopkinson, Matthew N.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) : 15545 - 15549
  • [40] Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products
    Mateus-Ruiz, Jeferson B.
    Cordero-Vargas, Alejandro
    SYNTHESIS-STUTTGART, 2020, 52 (21): : 3111 - 3128
12345