Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C-H activation and C-C bond cleavage

被引:26
|
作者
Yang, Wei [1 ,2 ]
Zhang, Haonan [1 ]
Liu, Yu [1 ,2 ]
Tang, Cuiman [1 ]
Xu, Xiaohui [1 ]
Liu, Jiaqi [1 ]
机构
[1] Northeast Elect Power Univ, Sch Chem Engn, Jilin 132012, Jilin, Peoples R China
[2] Gongqing Inst Sci & Technol, Gongqing 332020, Peoples R China
关键词
All Open Access; Gold;
D O I
10.1039/d2ra02074b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A redox-neutral synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones has been realized via Rh(iii)-catalyzed cascade C-H activation annulation. A possible Rh(iii)-Rh(v)-Rh(iii) mechanism involving an unprecedented beta-C elimination step was proposed.
引用
收藏
页码:14435 / 14438
页数:4
相关论文
共 50 条
  • [1] Rh(III)-catalyzed oxidative C-H bond arylation with hydroquinones: sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones
    Yang, Wei
    Wang, Shan
    Zhang, Qian
    Liu, Qun
    Xu, Xianxiu
    CHEMICAL COMMUNICATIONS, 2015, 51 (04) : 661 - 664
  • [2] Rh(<sc>iii</sc>)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation
    Dash, Om Prakash
    Garg, Divya
    Volla, Chandra M. R.
    CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10576 - 10579
  • [3] Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C-H/C-C bond activation
    Cui, Yixin
    Bai, Dachang
    Liu, Bingxian
    Chang, Junbiao
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2020, 56 (100) : 15631 - 15634
  • [4] Rh(iii)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C-H/C-C bond activation
    Hu, Hong
    Li, Bin-Shi
    Xu, Jing-Lei
    Sun, Wei
    Wang, Yong
    Sun, Meng
    CHEMICAL COMMUNICATIONS, 2022, 58 (30) : 4743 - 4746
  • [5] Rh(iii)-Catalyzed sequentialortho-C-H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones
    Dong, Yaqun
    Yu, Jin-Tao
    Sun, Song
    Cheng, Jiang
    CHEMICAL COMMUNICATIONS, 2020, 56 (49) : 6688 - 6691
  • [6] Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation
    Zhang, Yan-Bo
    Li, Bin-Shi
    Xu, Guo-Jie
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2023, 25 (21) : 3922 - 3926
  • [7] Rh(III)-Catalyzed Synthesis of N-Unprotected Indoles from Imidamides and Diazo Ketoesters via C-H Activation and C-C/C-N Bond Cleavage
    Qi, Zisong
    Yu, Songjie
    Li, Xingwei
    ORGANIC LETTERS, 2016, 18 (04) : 700 - 703
  • [8] Direct C-H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C-C Bond Cleavage of Cyclobutanone Oximes
    Gu, Yu-Rui
    Duan, Xin-Hua
    Yang, Lin
    Guo, Li-Na
    ORGANIC LETTERS, 2017, 19 (21) : 5908 - 5911
  • [9] Zirconium-Catalyzed Synthesis of 6-(Trifluoromethyl)-2H-pyran-2-ones via C-C Bond Cleavage
    Zhang, Zipeng
    Huang, Yangjie
    Yuan, Zihang
    Xia, Jianrong
    Weng, Zhiqiang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (08): : 5683 - 5689
  • [10] Rh(III)- and Ir(III)-Catalyzed C-C Bond Cross Couplings from C-H Bonds
    Wencel-Delord, Joanna
    Patureau, Frederic W.
    Glorius, Frank
    C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION I, 2016, 55 : 1 - 27