Annulation of Benzamides with Arynes Using Palladium with Photoredox Dual Catalysis

被引:29
|
作者
Zhao, Jie [1 ]
Li, Hongji [1 ]
Li, Pinhua [1 ]
Wang, Lei [1 ,2 ]
机构
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 14期
基金
美国国家科学基金会;
关键词
VISIBLE-LIGHT PHOTOREDOX; SINGLE-ELECTRON TRANSMETALATION; CARBON-CARBON; BOND; ARYLATION; ACTIVATION; INSERTION; BENZYNE; ACCESS; AMINES;
D O I
10.1021/acs.joc.9b00893
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient annulation of benzamides with arynes using palladium and photoredox dual catalysis under an oxygen atmosphere is disclosed, which circumvents the use of external toxic metal oxidant and proceeds readily via aryne insertion at room temperature to construct the phenanthridinone backbone.
引用
收藏
页码:9007 / 9016
页数:10
相关论文
共 50 条
  • [1] Enantioselective reductive allylic alkylation enabled by dual photoredox/palladium catalysis
    Tang, Sheng
    Zhang, Hong-Hao
    Yu, Shouyun
    CHEMICAL COMMUNICATIONS, 2023, 59 (09) : 1153 - 1156
  • [2] Visible-Light Photoredox and Palladium Dual Catalysis in Organic Synthesis
    Zhou, Wenjun
    Jiang, Yuanxu
    Chen, Liang
    Liu, Kaixing
    Yu, Dagang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3697 - 3713
  • [3] Dual Cobalt and Photoredox Catalysis Enabled Redox-Neutral Annulation of 2-Propynolphenols
    Zhu, Yao
    He, Yong-Qin
    Tian, Wan-Fa
    Wang, Mei
    Zhou, Zhao-Zhao
    Song, Xian-Rong
    Ding, Hai-Xin
    Xiao, Qiang
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) : 3372 - 3377
  • [4] Regio- and Enantioselective Decarboxylative Allylic Benzylation Enabled by Dual Palladium/Photoredox Catalysis
    Song, Changhua
    Zhang, Hong-Hao
    Yu, Shouyun
    ACS CATALYSIS, 2022, 12 (02) : 1428 - 1432
  • [5] Mechanistic explorations on the decarboxylative allylation of amino esters via dual photoredox and palladium catalysis
    Chen, Qingqing
    Zhang, Ruizhong
    Dang, Yanfeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (06) : 1138 - 1142
  • [6] Synthesis of π-extended dibenzo[d,k]ullazines by a palladium-catalyzed double annulation using arynes
    Wang, Deping
    Liu, Yan
    Wang, Linhua
    Cheng, Hu
    Zhang, Yuming
    Gao, Ge
    CHINESE CHEMICAL LETTERS, 2021, 32 (04) : 1407 - 1410
  • [7] Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls
    Liu, Zhijian
    Zhang, Xiaoxia
    Larock, Richard C.
    Journal of the American Chemical Society, 2005, 127 (45): : 15716 - 15717
  • [8] Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls
    Liu, ZJ
    Zhang, XX
    Larock, RC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) : 15716 - 15717
  • [9] Synthesis of π-extended dibenzo[d,k]ullazines by a palladium-catalyzed double annulation using arynes
    Deping Wang
    Yan Liu
    Linhua Wang
    Hu Cheng
    Yuming Zhang
    Ge Gao
    Chinese Chemical Letters, 2021, 32 (04) : 1407 - 1410
  • [10] Palladium-catalyzed decarbonylative annulation of phthalimides with arynes: direct construction of phenanthridinones
    Meng, Yan-Yu
    Si, Xiao-Ju
    Song, Yuan-Yuan
    Zhou, Hui-Min
    Xu, Fen
    CHEMICAL COMMUNICATIONS, 2019, 55 (64) : 9507 - 9510