Ir(III)-catalyzed C-H alkenylation/annulation of N-iminopyridinium ylides with acrylates and alkynes

被引:0
作者
Chen, Xiaopei [1 ]
Ma, Zhiwei [1 ]
Wang, Chuanchuan [1 ]
Hou, Xuehui [1 ]
Liu, Juntao [1 ]
机构
[1] Henan Univ Anim Husb & Econ, Fac Sci, 2 Yingcai St, Zhengzhou 450044, Henan, Peoples R China
关键词
Ir(III) catalysis; C-H bond activation; Alkenylation; Annulation; Oxidant free; N-Iminopyridinium ylides; BOND FORMATION; ISOQUINOLONE SYNTHESIS; INTERNAL OXIDANT; O BOND; ACTIVATION; CYCLIZATION; OLEFINATION; ARYLATION; CARBON; ROUTE;
D O I
10.1016/j.tet.2024.134322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient protocol for Ir(III)-catalyzed ortho-alkenylation and annulation of N-iminopyridinium ylides with acrylates and alkynes has been developed, providing o-alkenyl benzamides and isoquinolones in good to excellent yields. This reaction proceeds well under external oxidant free conditions with high practicality and efficiency, and broad functional group tolerance.
引用
收藏
页数:10
相关论文
共 56 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] ang J.Y., 2019, Org. Lett., V21, P9904
  • [3] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [4] Ir(III)-Catalyzed Mono-Olefination of Aryl C-H Bonds Using -SCF3 as a Weak Directing Group
    Bao, Rui-Peng
    Chen, Xian
    Li, Chen
    Wang, Dong-Hui
    [J]. ORGANIC LETTERS, 2019, 21 (19) : 8116 - 8121
  • [5] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [6] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides
    Bellina, Fabio
    Rossi, Renzo
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 1082 - 1146
  • [7] Selective activation of apoptosis by a novel set of 4-aryl-3-(3-aryl-1-oxo-2-propenyl)-2(1H)-quinolinones through a Myc-dependent pathway
    Claassen, Gisela
    Brin, Elena
    Crogan-Grundy, Candace
    Vaillancourt, Mei Ting
    Zhang, Han Zhong
    Cai, Sui Xiong
    Drewe, John
    Tseng, Ben
    Kasibhatla, Shailaja
    [J]. CANCER LETTERS, 2009, 274 (02) : 243 - 249
  • [8] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
    Colby, Denise A.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
  • [9] C-H Bond Activation Reactions of Ethers That Generate Iridium Carbenes
    Conejero, Salvador
    Paneque, Margarita
    Poveda, Manuel L.
    Santos, Laura L.
    Carmona, Ernesto
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) : 572 - 580
  • [10] Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C-H/N-N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media
    Deshmukh, Dewal S.
    Gangwar, Neha
    Bhanage, Bhalchandra M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (18) : 2919 - 2927