Thianthrenium-Enabled Phosphorylation of Aryl C-H Bonds via Electron Donor-Acceptor Complex Photoactivation

被引:41
|
作者
Xu, Hao [1 ]
Li, Xufeng [2 ]
Dong, Yuzheng [1 ]
Ji, Shuangran [1 ]
Zuo, Junze [1 ]
Lv, Jian [1 ]
Yang, Daoshan [1 ,3 ]
机构
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Key Lab Opt Elect Sensing & Analyt Chem Life Sci, MOE, Qingdao 266042, Peoples R China
[2] Zhejiang Wansheng Co Ltd, Linhai 317000, Zhejiang, Peoples R China
[3] Nanjing Forestry Univ, Natl Engn Res Ctr Low Carbon Proc & Utilizat Fores, Nanjing 210037, Peoples R China
基金
中国国家自然科学基金;
关键词
PHOTOREDOX CATALYSIS; FUNCTIONALIZATION; ARYLATION; SULFONYLATION; ALKYLATION; ARENES; SALTS; OXIDE;
D O I
10.1021/acs.orglett.3c01303
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anefficient strategy for the preparation of aryl phosphonatesvia blue-light-promoted single electron transfer process of an EDAcomplex between phosphites and thianthrenium salts has been demonstrated.The corresponding substituted aryl phosphonates were obtained in goodto excellent yields, and the byproduct thianthrene can be recoveredand reused in quantity. This developed method realizes the constructionof aryl phosphonates through the indirect C-H functionalizationof arenes, which has potential application value in drug discoveryand development.
引用
收藏
页码:3784 / 3789
页数:6
相关论文
共 50 条
  • [41] A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes
    de Pedro Beato, Eduardo
    Spinnato, Davide
    Zhou, Wei
    Melchiorre, Paolo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (31) : 12304 - 12314
  • [42] Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation
    Polites, Viktor C.
    Badir, Shorouk O.
    Keess, Sebastian
    Jolit, Anais
    Molander, Gary A.
    ORGANIC LETTERS, 2021, 23 (12) : 4828 - 4833
  • [43] Visible-Light-Mediated (sp3)Cα-H Functionalization of Ethers Enabled by Electron Donor-Acceptor Complex
    Roy, Sourav
    Chatterjee, Indranil
    ACS ORGANIC & INORGANIC AU, 2022, 2 (04): : 306 - 311
  • [44] Electron donor-acceptor complex enabled cascade reaction of unprotected o-anilide aryl chlorides for heterocycle synthesis
    Yang, Zhu-Sheng
    Tang, Wen-Xin
    Zhang, Bei-Bei
    Sun, De-Qun
    Chen, Kun-Quan
    Chen, Xiang-Yu
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1219 - 1223
  • [45] DIFFERENT BEHAVIOR OF C=N AND C=O BONDS IN FORMATION OF DONOR-ACCEPTOR COMPLEX
    SCHONFELD, P
    DORING, I
    JAHNKE, D
    REINHECKEL, H
    ZEITSCHRIFT FUR CHEMIE, 1976, 16 (01): : 22 - 23
  • [46] A catalyst- and thiol-free protocol for arene C-H thioetherification via photoactive electron donor-acceptor complexes
    Gao, Ang
    Liu, He-Xiang
    Zhou, Ya-Nan
    Fu, Ming-Chen
    GREEN CHEMISTRY, 2025, 27 (08) : 2286 - 2292
  • [47] An electron donor–acceptor photoactivation strategy for the synthesis of S-aryl dithiocarbamates using thianthrenium salts under mild aqueous micellar conditions
    Hao Xu
    Xufeng Li
    Jie Ma
    Junze Zuo
    Xiuyan Song
    Jian Lv
    Daoshan Yang
    Chinese Chemical Letters, 2023, 34 (11) : 143 - 149
  • [48] Regioselective Double C-H Functionalization of Arenes via Aryl Thianthrenium Salt Analogues
    Hamad, Aboubakr
    Mrozowicz, Michal
    Xie, Yuanhao
    Ritter, Tobias
    SYNLETT, 2024, 35 (09) : 1028 - 1032
  • [49] C4-Selective C-H Borylation of Pyridinium Derivatives Driven by Electron Donor-Acceptor Complexes
    Choi, Wonjun
    Kim, Minseok
    Lee, Kangjae
    Park, Seongjin
    Hong, Sungwoo
    ORGANIC LETTERS, 2022, 24 (51) : 9452 - 9457
  • [50] A visible-light-catalyzed sulfonylation reaction of an aryl selenonium salt via an electron donor-acceptor complex
    Wang, Yuqing
    Zhao, Liang
    Hao, Xinyu
    Jin, Kun
    Zhang, Rong
    Duan, Chunying
    Li, Yaming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (12) : 2451 - 2455