Rh(<sc>iii</sc>)-catalyzed regioselective C(sp2)-H alkenylation of isoquinolones with methoxyallene: A facile access to aldehyde-bearing isoquinolones

被引:1
|
作者
Thakur, Ankita [1 ,2 ]
Chandra, Devesh [1 ]
Sharma, Upendra [1 ,2 ]
机构
[1] CSIR IHBT, Chem Technol Div, C H Activat & Phytochemistry Lab, Palampur 176061, Himachal Prades, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
C-H ACTIVATION; ALLENES; FUNCTIONALIZATIONS; ALKOXYALLENES; ALLYLATION; REACTIVITY; ARENES;
D O I
10.1039/d4ob01084a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and rapid access to isoquinolone aldehyde scaffolds has been established by a rhodium-catalyzed reaction between isoquinolone and methoxyallene that forges alkenylation in an explicit regioselective manner. Herein, methoxyallene serving as an acrolein equivalent results in execution of this unique functionalization. Furthermore, the compatibility with complex molecules underscores the significance of this developed protocol. The mechanistic proposal for this regioselective transformation was consistent with kinetic studies and several control reactions.
引用
收藏
页码:6612 / 6616
页数:5
相关论文
共 50 条
  • [41] Rhodium(III)-Catalyzed Heteroannulations of 3-Sulfolene Derivatives through C(sp2)-H Activation: Access to Pyridine ortho-Quinodimethane Precursors
    Saiegh, Tomas J.
    Meyer, Christophe
    Cossy, Janine
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (22)
  • [42] Tunable Rh(III)-Catalyzed C(sp2)-H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups
    Junnan, E.
    Wang, Luohe
    Zeng, Jing
    Tian, Hua
    Bu, Xiubin
    Yang, Xiaobo
    Zhao, Zhen
    ORGANIC LETTERS, 2024, 26 (37) : 7885 - 7890
  • [43] A cascade indazolone-directed Ir(iii)- and Rh(iii)-catalyzed C(sp2)-H functionalization/[4 + 2] annulation of 1-arylindazolones with sulfoxonium ylides to access chemically divergent 8H-indazolo [1,2-a]cinnolines
    Zheng, Yi-Chuan
    Shu, Bing
    Zeng, Yao-Fu
    Chen, Shao-Yong
    Song, Jia-Lin
    Liu, Yan-Zhi
    Xiao, Lin
    Liu, Xu-Ge
    Zhang, Xuanxuan
    Zhang, Shang-Shi
    Organic Chemistry Frontiers, 2022, 9 (19) : 5185 - 5190
  • [44] Synthesis of Naphthoquinolizinones through Rh(III)-Catalyzed Double C(sp2)-H Bond Carbenoid Insertion and Annulation of 2-Aryl-3-cyanopyridines with α-Diazo Carbonyl Compounds
    Zhang, Beibei
    Li, Bin
    Zhang, Xin-Ying
    Fan, Xuesen
    ORGANIC LETTERS, 2017, 19 (09) : 2294 - 2297
  • [45] Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[b]carbazoles via Dual C(sp2)-H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes
    Li, Qiuyun
    Wang, Yanwei
    Li, Bin
    Wang, Baiquan
    ORGANIC LETTERS, 2018, 20 (24) : 7884 - 7887
  • [46] Amide-Directed Alkenylation of sp2 C-H Bonds Catalyzed by a Cationic Rh(I)/BIPHEP Complex Under Mild Conditions: Dramatic Rate Acceleration by a 1-Pyrrolidinecarbonyl Group
    Shibata, Yu
    Otake, Yousuke
    Hirano, Masao
    Tanaka, Ken
    ORGANIC LETTERS, 2009, 11 (03) : 689 - 692
  • [47] Ni(II)-catalyzed C(sp2) -H alkynylation/annulation cascades: Regioselective access to 3-methyleneisoindoline-1-one using N,S-bidentate auxiliary
    Chen, Su-Qin
    Jiao, Jun-Ying
    Zhang, Xing-Guo
    Zhang, Xiao-Hong
    TETRAHEDRON, 2019, 75 (02) : 246 - 252
  • [48] A cascade indazolone-directed Ir(iii)- and Rh(iii)-catalyzed C(sp2)-H functionalization/[4+2] annulation of 1-arylindazolones with sulfoxonium ylides to access chemically divergent 8H-indazolo [1,2-a]cinnolines
    Zheng, Yi-Chuan
    Shu, Bing
    Zeng, Yao-Fu
    Chen, Shao-Yong
    Song, Jia-Lin
    Liu, Yan-Zhi
    Xiao, Lin
    Liu, Xu-Ge
    Zhang, Xuanxuan
    Zhang, Shang-Shi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19): : 5185 - 5190
  • [49] Rh(III)-Catalyzed [3+2] Annulation of Aniline Derivatives with Vinylsilanes via C-H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives
    Khake, Shrikant M.
    Chatani, Naoto
    ACS CATALYSIS, 2021, 11 (19): : 12375 - 12383
  • [50] Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C-H Activation-Lossen Rearrangement-Wallach Reaction
    Tan, Jin-Fay
    Bormann, Carl Thomas
    Severin, Kay
    Cramer, Nicolai
    ACS CATALYSIS, 2020, 10 (06) : 3790 - 3796