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
来源：
GREEN CHEMISTRY | 2021年 / 23卷 / 04期
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
  • [41] Visible light mediated, metal-free carbene transfer reactions of diazoalkanes with propargylic alcohols
    He, Feifei
    Koenigs, Rene M.
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (33) : 4881 - 4884
  • [42] Metal-Free Synthesis of Guanidines from Thioureas in Water Reactions Mediated by Visible Light
    Annuur, Rose Malina
    Saetan, Trin
    Sukwattanasinitt, Mongkol
    Wacharasindhu, Sumrit
    [J]. SYNTHESIS-STUTTGART, 2023, 55 (14): : 2166 - 2176
  • [43] Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
    Meyer, Andreas U.
    Slanina, Tomas
    Yao, Chang-Jiang
    Koenig, Burkhard
    [J]. ACS CATALYSIS, 2016, 6 (01): : 369 - 375
  • [44] Isotruxene-based porous polymers as efficient and recyclable photocatalysts for visible-light induced metal-free oxidative organic transformations
    Zhang, Haowen
    Zhou, Cen
    Zheng, Ying
    Zhang, Xiao
    [J]. GREEN CHEMISTRY, 2021, 23 (22) : 8878 - 8885
  • [45] Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water
    Jana, Sadhan
    Verma, Ajay
    Kadu, Rahul
    Kumar, Sangit
    [J]. CHEMICAL SCIENCE, 2017, 8 (09) : 6633 - 6644
  • [46] Metal-free oxidative phosphinylation of aryl alkynes to β-ketophosphine oxides via visible-light photoredox catalysis
    Bu, Mei-jie
    Lu, Guo-ping
    Cai, Chun
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (02) : 413 - 416
  • [47] Metal-free heterojunction of graphitic carbon nitride composite with superior and stable visible-light active photocatalysis
    Sundaram, Induja M.
    Kalimuthu, Sivaprakash
    Priya, P. Gomathi
    [J]. MATERIALS CHEMISTRY AND PHYSICS, 2018, 204 : 243 - 250
  • [48] Metal-Free Porphyrin-Sensitized Mesoporous Titania Films For Visible-Light Indoor Air Oxidation
    Ismail, Adel A.
    Bahnemann, Detlef W.
    [J]. CHEMSUSCHEM, 2010, 3 (09) : 1057 - 1062
  • [49] Biowaste-derived hydrochar microspheres: Realizing metal-free visible-light photocatalytic oxidation of amines
    Su, Feng
    Peng, Haoyu
    Yin, Hui
    Luo, Chao
    Zhu, Lixia
    Zhong, Wenzhou
    Mao, Liqiu
    Yin, Dulin
    [J]. JOURNAL OF CATALYSIS, 2021, 404 : 149 - 162
  • [50] Metal-free polymeric and molecular disorder/order semiconductor heterojunctions for the visible-light photocatalytic Minisci reaction
    Li, Peihe
    Li, Qingguang
    Wang, Gelan
    Lu, Ye
    Duan, Limei
    Bai, Jie
    Sarina, Sarina
    Liu, Jinghai
    [J]. JOURNAL OF MATERIALS CHEMISTRY A, 2024, 12 (23) : 13760 - 13769
12345