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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 32期
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 54 条
  • [1] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes
    Aubert, Corinne
    Fensterbank, Louis
    Garcia, Pierre
    Malacria, Max
    Simonneau, Antoine
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1954 - 1993
  • [2] Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
    Casanova, Noelia
    Del Rio, Karina P.
    Garcia-Fandino, Rebeca
    Mascarenas, Jose L.
    Gulias, Moises
    [J]. ACS CATALYSIS, 2016, 6 (05): : 3349 - 3353
  • [3] Chemo selective C-H alkylation of isoquinolones with maleimides: A combined experimental and computational case study
    Chandra, Devesh
    Kumar, Nikunj
    Sumit, Puneet
    Gupta, Puneet
    Sharma, Upendra
    [J]. MOLECULAR CATALYSIS, 2023, 551
  • [4] Co(iii)-catalysed regioselective linear C(8)-H olefination of isoquinolone with terminal aromatic and aliphatic alkynes
    Chandra, Devesh
    Kumar, Nikunj
    Sumit
    Parmar, Diksha
    Gupta, Puneet
    Sharma, Upendra
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (88) : 11613 - 11616
  • [5] Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes
    Chen, Shi-Yong
    Li, Qingjiang
    Wang, Honggen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) : 11173 - 11181
  • [6] Iridium(III)-Catalyzed Regiocontrolled Direct Amidation of Isoquinolones and Pyridones
    Das, Debapratim
    Samanta, Rajarshi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) : 379 - 384
  • [7] [PdCl2(MeCN)2]-Catalyzed Highly Regio- and Stereoselective Allylation of Electron-Rich Arenes with 2,3-Allenoates
    Fang, Zhao
    Fu, Chunling
    Ma, Shengming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) : 3910 - 3913
  • [8] Acrolein environmental levels and potential for human exposure
    Faroon, O.
    Roney, N.
    Taylor, J.
    Ashizawa, A.
    Lumpkin, M. H.
    Plewak, D. J.
    [J]. TOXICOLOGY AND INDUSTRIAL HEALTH, 2008, 24 (08) : 543 - 564
  • [9] Rh(III)-Catalyzed C-H Activation with Allenes To Synthesize Conjugated Olefins
    Gong, Tian-Jun
    Su, Wei
    Liu, Zhao-Jing
    Cheng, Wan-Min
    Xiao, Bin
    Fu, Yao
    [J]. ORGANIC LETTERS, 2014, 16 (02) : 330 - 333
  • [10] A short chemoenzymatic synthesis of (+)-narciclasine
    Gonzalez, D
    Martinot, T
    Hudlicky, T
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3077 - 3080
123456