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
  • [21] Rhodium(III)-Catalyzed C(sp2)-H Functionalization of Cyclobutenes. Access to Cyclobuta[c]pyridones and -pyridines
    Saiegh, Tomas J.
    Chedotal, Henri
    Meyer, Christophe
    Cossy, Janine
    ORGANIC LETTERS, 2019, 21 (20) : 8364 - 8368
  • [22] Rh(iii)-Catalyzed C(sp2)-H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives
    Han, Zhi-Peng
    Xu, Meng-Meng
    Zhang, Rui-Ying
    Xu, Xiao-Ping
    Ji, Shun-Jun
    GREEN CHEMISTRY, 2021, 23 (17) : 6337 - 6340
  • [23] Cp*Ir(iii)- and Cp*Rh(iii)-catalyzed C(sp2)-H amination of arenes using thioethers as directing groups
    Xie, Hui
    Zhong, Mei
    Wang, Xiao-Tong
    Wu, Jia-Qiang
    Cai, Yan-Qu
    Liu, Jidan
    Shu, Bing
    Che, Tong
    Zhang, Shang-Shi
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (03): : 635 - 642
  • [24] Iridium(III)-catalyzed β-trifluoromethyl enone carbonyl-directed regioselective ortho-C(sp2)-H olefination
    Sindhe, Haritha
    Kamble, Akshay
    Reddy, Malladi Mounika
    Singh, Amardeep
    Sharma, Satyasheel
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (06) : 1162 - 1166
  • [25] Rh(III)-Catalyzed C(sp2)-H and C(sp2)-C(sp2) Bond Activation of Aryl Oximes with CF3-Imidoyl Sulfoxonium Ylides: Access to N-(2-Cyanoaryl)-3-(Trifluoromethyl)isoquinolin-1(2H)-Imines
    Li, Pinyi
    Chen, Jian
    Yang, Zuguang
    Chen, Zhengkai
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [26] C(sp2)-H selenylation of substituted benzo[4,5]imidazo[2,1-b]thiazoles using phenyliodine(<sc>iii</sc>)bis(trifluoroacetate) as a mediator
    Ghosh, Prasanjit
    Chhetri, Gautam
    Mandal, Anirban
    Chen, Yu
    Hersh, William H.
    Das, Sajal
    RSC ADVANCES, 2024, 14 (07) : 4462 - 4470
  • [27] Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(<sc>iii</sc>)-catalyzed cascade C-H functionalization/[3+2] dipolar cycloaddition
    Liu, Fu-Xiaomin
    Chen, Weijie
    Cai, Ying
    Zhou, Zhi
    Yi, Wei
    Cheng, Kui
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (09) : 2512 - 2517
  • [28] Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C-H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines
    Liu, Xingyan
    Li, Xiaoyu
    Liu, Hu
    Guo, Qiang
    Lan, Jingbo
    Wang, Ruilin
    You, Jingsong
    ORGANIC LETTERS, 2015, 17 (12) : 2936 - 2939
  • [29] Reverse Regioselective Cp*Co(III)-Catalyzed [4+2] C-H Annulation of N-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities
    Ghosh, Arijit
    Rana, Tamanna
    Bhaduri, Nilanjan
    Pawar, Amit B.
    ORGANIC LETTERS, 2023, 25 (43) : 7878 - 7883
  • [30] One-Pot Cascade Access to Ru(II)-Catalyzed Regioselective C(sp2)-H Activation/Alkenylation of Chromeno[4,3-c]pyrazol-4-ones and Their Emission Solvatochromic Studies
    Singla, Dinesh
    Paul, Kamaldeep
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16436 - 16448