Ru(II)-Catalyzed Tunable Cascade Reaction via C-H/C-C Bond Cleavage

被引:17
|
作者
Yang, Zi [1 ]
Yue, Qi [1 ]
Yang, Mengqi [1 ]
Zhang, Hong [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Dept Engn,Sch Biomed Sci, Res Ctr Mol Med,Key Lab Precis Med & Mol Diag Fuj, Minist Educ,Key Lab Fujian Mol Med,Key Lab Xiamen, Xiamen 361021, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 20期
关键词
H ACTIVATION; FUNCTIONALIZATION; CYCLIZATION; ANNULATION; DEUTERIUM; EFFICIENT; ALKYNES; NITRILES; STRATEGY;
D O I
10.1021/acs.joc.0c01614
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile synthesis of various 3-(alkoxyalkyl)-1H-indoles from pyrazolidinones, 2-acetylenic ketones, and alkyl alcohols via C-H/C-C bond activation has been developed. The reaction proceeds smoothly under the proper reaction conditions, and preliminary mechanistic studies suggest that NaOAc is crucial for C-C bond activation. The advantages of the present method represent a redox-neutral process and exhibit excellent chemo and regioselectivity.
引用
收藏
页码:12960 / 12970
页数:11
相关论文
共 50 条
  • [21] Ruthenium(II)-catalyzed α-fluoroalkenylation of arenes via C-H bond activation and C-F bond cleavage
    Li, Na
    Chang, Junbiao
    Kong, Lingheng
    Li, Xingwei
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (12): : 1978 - 1982
  • [22] Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation
    Zhang, Yan-Bo
    Li, Bin-Shi
    Xu, Guo-Jie
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2023, 25 (21) : 3922 - 3926
  • [23] Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols
    Wang, Siqi
    Miao, Erfei
    Wang, Hao
    Song, Bichao
    Huang, Wei
    Yang, Weibo
    CHEMICAL COMMUNICATIONS, 2021, 57 (48) : 5929 - 5932
  • [24] Mechanistic study of oxidative C-H and C-C bond cleavage of ethane
    Kattel, Shyam
    Chen, Jingguang
    Liu, Ping
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [25] Transition-Metal-Catalyzed C-C Bond Macrocyclization via Intramolecular C-H Bond Activation
    Wang, Xiao
    Lu, Ming-Zhu
    Loh, Teck-Peng
    CATALYSTS, 2023, 13 (02)
  • [26] Oxidative ortho-amino-methylation of phenols via C-H and C-C bond cleavage
    Sun, Wenbo
    Lin, Huacan
    Zhou, Wenyu
    Li, Zigang
    RSC ADVANCES, 2014, 4 (15) : 7491 - 7494
  • [27] Gold(I)-Catalyzed Tandem C-H and C-C Activation (Cleavage)
    Jiang, Min
    Liu, Le-Ping
    Shi, Min
    Li, Yuxue
    ORGANIC LETTERS, 2010, 12 (01) : 116 - 119
  • [28] Cu(II)-Mediated C-C/C-O Bond Formation via C-H/C-C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
    Yu, Shuling
    Lv, Ningning
    Liu, Zhanxiang
    Zhang, Yuhong
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 118 - 125
  • [29] C-H activation and subsequent C-C bond formation in rigid alkenes catalyzed by Ru(III) metallates
    Dharani, S.
    Kalaiarasi, G.
    Lynch, Vincent M.
    Srinivasan, K.
    Prabhakaran, R.
    REACTION CHEMISTRY & ENGINEERING, 2022, 8 (01) : 164 - 174
  • [30] C-C Bond formation via double C-H functionalization
    DeBoef, Brenton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238