Pd and photoredox dual catalysis assisted decarboxylative ortho-benzoylation of N-phenyl-7-azaindoles

被引:12
|
作者
Rajput, Shruti [1 ]
Kaur, Ramandeep [1 ]
Jain, Nidhi [1 ]
机构
[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India
关键词
ALPHA-OXOCARBOXYLIC ACIDS; VISIBLE-LIGHT PHOTOCATALYSIS; C-H FUNCTIONALIZATION; KETO ACIDS; COUPLING REACTION; ACYLATION; 7-AZAINDOLES; DRIVEN; ARENES; ACYLARYLATION;
D O I
10.1039/d1ob02338a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The directing group assisted decarboxylative ortho-benzoylation of N-aryl-7-azaindoles with alpha-keto acids has been achieved by synergistic visible light promoted photoredox and palladium catalysis. The approach tenders rapid entry to aryl ketone architectures from simple alpha-keto acid precursors via the in situ generation of a benzoyl radical intermediate. The transformation provides a range of ortho-benzoylated N-aryl-7-azaindoles, with excellent site-selectivity and good functional group compatibility under mild reaction conditions. Biological target predictions indicate that these molecules may serve as potential anti-cancer and anti-viral agents.
引用
收藏
页码:1453 / 1461
页数:9
相关论文
共 10 条
  • [1] Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
    Yufan Liang
    Xiaheng Zhang
    David W. C. MacMillan
    Nature, 2018, 559 : 83 - 88
  • [2] Decarboxylative Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual Catalysis
    Cartwright, Kaitie C.
    Tunge, Jon A.
    ACS CATALYSIS, 2018, 8 (12): : 11801 - 11806
  • [3] Rhodium(III)-catalyzed Mono- and Dialkenylation of N-Phenyl-7-azaindoles via Regioselective C-H Bond Cleavage
    Morioka, Ryosuke
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2016, 45 (06) : 682 - 684
  • [4] Decarboxylative sp3 C-N coupling via dual copper and photoredox catalysis
    Liang, Yufan
    Zhang, Xiaheng
    MacMillan, David W. C.
    NATURE, 2018, 559 (7712) : 83 - +
  • [5] Decarboxylative sp3 C-N coupling via dual copper/photoredox catalysis
    Liang, Yufan
    Zhang, Xiaheng
    MacMillan, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [6] Regio- and Diastereoselective Decarboxylative Allylation of N-Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis
    Zheng, Jun
    Nopper, Christoph
    Bibi, Rifhat
    Nikbakht, Ali
    Bauer, Felix
    Breit, Bernhard
    ACS CATALYSIS, 2022, 12 (10) : 5949 - 5960
  • [7] RETRACTION: Heterogeneous Titania-Photoredox/Nickel Dual Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Aryl Iodides (Retraction of Vol 7, Pg 2171, 2017)
    McTiernan, Christopher D.
    Leblanc, Xavier
    Scaiano, Juan C.
    ACS CATALYSIS, 2018, 8 (10): : 9847 - 9847
  • [8] Mechanistic Study on the Decarboxylative sp3 C-N Cross-Coupling between Alkyl Carboxylic Acids and Nitrogen Nucleophiles via Dual Copper and Photoredox Catalysis
    Zhao, Xia
    Liu, Yanhong
    Zhu, Rongxiu
    Liu, Chengbu
    Zhang, Dongju
    INORGANIC CHEMISTRY, 2019, 58 (19) : 12669 - 12677
  • [9] Visible-Light-Driven Regioselective Decarboxylative Acylation of N-Methyl-3-phenylquinoxalin-2(1H)-one by Dual Palladium-Photoredox Catalysis Through C-H Activation
    Kumar, Prashant
    Singh, Brajendra Kumar
    ACS OMEGA, 2023, 9 (01): : 651 - 657
  • [10] Alkynylation of N-(3-iodopyridin-2-yl)sulfonamide under Pd/C-Cu catalysis: a direct one pot synthesis of 7-azaindoles and their pharmacological evaluation as potential inhibitors of sirtuins
    Layek, Mohosin
    Kumar, Y. Syam
    Islam, Aminul
    Karavarapu, Ravikumar
    Sengupta, Amrita
    Halder, Devyani
    Mukkanti, K.
    Pal, Manojit
    MEDCHEMCOMM, 2011, 2 (06) : 478 - 485