Visible-light induced metal-free cascade Wittig/hydroalkylation reactions

被引:17
|
作者
Miao, Pannan [1 ]
Li, Ruining [1 ]
Lin, Xianfeng [1 ]
Rao, Liangming [2 ,3 ]
Sun, Zhankui [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Pharm, Pharma X Ctr, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Chinese Acad Sci, Huzhou Res & Ind Ctr Technol, 1366 Hongfeng Rd, Huzhou 313000, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Nutr & Hlth, 320 Yueyang Rd, Shanghai 200031, Peoples R China
关键词
WITTIG;
D O I
10.1039/d1gc00091h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cascade reactions are green and powerful transformations for building multiple carbon-carbon bonds in one step. Through a relay olefination and radical addition process, we were able to develop the cascade Wittig/hydroalkylation reactions induced by visible light. This metal-free radical approach features mild conditions, robustness, and excellent functionality compatibility. It allows access to saturated C3 homologation products directly from aldehydes or ketones. The synthetic utility of this method is demonstrated by a two-step synthesis of indolizidine 209D.
引用
收藏
页码:1638 / 1641
页数:4
相关论文
共 50 条
  • [1] Metal-Free Synthesis of Diarylmethanes through Visible-Light Induced Radical Reactions with Arylamines
    Wang, Youjia
    Duan, Ruochen
    Wu, Yanhui
    Li, Xulian
    Deng, Chao
    [J]. CHEMISTRYSELECT, 2021, 6 (24): : 6097 - 6101
  • [2] Metal-Free Visible-Light-Induced Trifluoromethylation Reactions
    Park, Gwi-Rim
    Choi, Yeojin
    Choi, Myung Gil
    Chang, Suk-Kyu
    Cho, Eun Jin
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) : 436 - 440
  • [3] Visible-Light Driven, Metal-Free Hydroalkylation of Alkenes Mediated by Electron Donor-Acceptor Complex Using Benzothiazolines
    Uchikura, Tatsuhiro
    Fujii, Tatsuya
    Moriyama, Kaworuko
    Akiyama, Takahiko
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (12) : 2962 - 2966
  • [4] Metal-Free Difluoromethylselenolation of Arylamines Under Visible-Light Photocatalysis
    Lu, Kui
    Li, Quan
    Xi, Xiaolan
    Zhou, Ting
    Zhao, Xia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 1224 - 1231
  • [5] Visible light-induced metal-free cascade denitrogenative borylation and iodination of nitroarenes
    Li, Jun-Wei
    Duan, Tian-Shun
    Sun, Bing
    Zhang, Fang-Lin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (14) : 2819 - 2823
  • [6] Visible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes
    Tang, Nana
    Zachmann, Raphael J.
    Xie, Hui
    Zheng, Jun
    Breit, Bernhard
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (15) : 2122 - 2125
  • [7] A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light
    Qiu, Wenting
    Shi, Shuai
    Li, Ruining
    Lin, Xianfeng
    Rao, Liangming
    Sun, Zhankui
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (05) : 1255 - 1258
  • [8] Visible Light-Induced Metal-Free Fluoroalkylations
    Ka, Cheol Hyeon
    Kim, Seoyeon
    Cho, Eun Jin
    [J]. CHEMICAL RECORD, 2023, 23 (09):
  • [9] Pyrenedione as a metal-free visible-light photocatalyst for aerobic alkylation and epoxidation
    Zhang, Yuannian
    Wu, Jie
    Huang, Dejian
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [10] Metal-Free Visible-Light Radical Iodoperfluoroalkylation of Terminal Alkenes and Alkynes
    Yajima, Tomoko
    Ikegami, Mako
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2126 - 2129