Photocatalyst-Free Visible-Light Photoredox Dearomatization of Phenol Derivatives Containing Ketoximes: An Easy Access to Spiropyrrolines

被引：45
|
作者：
Han, Yongzhen [1 ]
Jin, Yunhe [1 ]
Jiang, Min [1 ]
Yang, Haijun [1 ]
Fu, Hua [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
基金：
中国国家自然科学基金;
关键词：
CATALYSIS; SPIRO; SPIROLACTONIZATION; FUNCTIONALIZATION; GENERATION; STRATEGIES; ARYLATION; SALTS; ACIDS;
D O I：
10.1021/acs.orglett.9b00372
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and simple visible-light photoredox intramolecular dearomatization of phenol derivatives containing ketoximes leading to spiropyrrolines has been developed. The protocol uses readily available 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the, base and electron-donor, visible light as the light source, and the reaction was performed well at room temperature without need of a photocatalyst. Therefore, the present method should provide a useful strategy for synthesis of spiropyrrolines.
引用
收藏
页码：1799 / 1803
页数：5
相关论文
共 29 条
  • [1] Visible-light-induced photocatalyst-free dearomative amidation of phenol derivatives
    Wu, Lingang
    Sun, Lei
    Liu, Wanxing
    Cui, Jichun
    Xie, Lei
    TETRAHEDRON LETTERS, 2023, 128
  • [2] Visible-light induced disproportionation of pyrrole derivatives for photocatalyst-free aryl halides reduction
    Li, Zhi-Jun
    Li, Shuya
    Hofman, Elan
    Davis, Andrew Hunter
    Leem, Gyu
    Zheng, Weiwei
    GREEN CHEMISTRY, 2020, 22 (06) : 1911 - 1918
  • [3] Visible-light promoted photocatalyst-free aerobic α-oxidation of tertiary amines to amides
    Xie, Xinpeng
    Guo, Xuan
    Qiao, Kaikai
    Shi, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8031 - 8036
  • [4] Visible-light promoted dithioacetalization of aldehydes with thiols under aerobic and photocatalyst-free conditions
    Xing, Zhimin
    Yang, Mingyang
    Sun, Haiyu
    Wang, Zemin
    Chen, Peng
    Liu, Lin
    Wang, Xiaolei
    Xie, Xingang
    She, Xuegong
    GREEN CHEMISTRY, 2018, 20 (22) : 5117 - 5122
  • [5] Visible-Light Photoredox Enables Ketone Carbonyl Alkylation for Easy Access to Tertiary Alcohols
    Minh Duy Vu
    Das, Mrinmoy
    Guo, Aoxin
    Ang, Zi-En
    Dokic, Milos
    Soo, Han Sen
    Liu, Xue-Wei
    ACS CATALYSIS, 2019, 9 (10) : 9009 - 9014
  • [6] Photocatalyst-Free Visible-Light Enabled Synthesis of Substituted Pyrroles from α-Keto Vinyl Azides
    Borra, Satheesh
    Borkotoky, Lodsna
    Newar, Uma Devi
    Das, Babulal
    Maurya, Ram Awatar
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (16) : 3364 - 3368
  • [7] Photocatalyst-free hydroacylations of electron-poor alkenes and enones under visible-light irradiation
    Palvoelgyi, Adam Mark
    Ehrschwendtner, Florian
    Schnuerch, Michael
    Bica-Schroeder, Katharina
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (36) : 7245 - 7249
  • [8] Photocatalyst-free regioselective sulfonamidation of N-(2-hydroxyaryl)amides in visible-light
    Rajat, Shruti
    Rajput, Shruti
    Grover, Nitika
    Jain, Nidhi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (43) : 8649 - 8655
  • [9] Visible-Light-Driven Metal-Free and Photocatalyst-Free Intramolecular Cyclization of Chalcones to Access Phenanthrenes
    Yi, Miaoyan
    Zhang, Chen
    Liao, Saihu
    Sun, Bing
    SYNLETT, 2025, 36 (03) : 274 - 278
  • [10] The Photocatalyst-Free Cross-Dehydrogenative Coupling Reaction Enabled by Visible-Light Direct Excitation of Substrate Xuan
    Guo, Xuan
    Shao, Bing-ru
    Jiang, Wen-feng
    Shi, Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15743 - 15752
123