Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates to access isoquinolines

被引:96
|
作者
Chu, Haoke [1 ]
Sun, Song [1 ]
Yu, Jin-Tao [1 ]
Cheng, Jiang [1 ]
机构
[1] Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Sch Petrochem Engn, Changzhou 213164, Peoples R China
基金
中国国家自然科学基金;
关键词
BETA-PHENYLETHYLAMINES; INTERNAL ALKYNES; BOND ACTIVATION; PAPAVERINE; FUNCTIONALIZATION; DERIVATIVES; CYCLIZATION; ALKALOIDS; KETIMINES; ESTERS;
D O I
10.1039/c5cc04708k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The concise synthesis of 3-substituted or non-C3-substituted isoquinolines through Rh-catalyzed sequential oxidative C-H activation/annulation with geminal-substituted vinyl acetates was developed with good functional group tolerance. The protocol was successfully applied to the total synthesis of the natural product papaverine.
引用
收藏
页码:13327 / 13329
页数:3
相关论文
共 50 条
  • [41] Mechanistic insights into rhodium-catalyzed C-H activation and annulation using vinyl acetate to access cinnolines and cinnolin-4(1H)-ones
    Wang, Yuqin
    Zeng, Yiling
    Tian, Ya-Nan
    Liu, Zheng
    Wang, Jinhua
    Chen, Shuyou
    Li, Shiqing
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (02): : 553 - 560
  • [42] Synthesis of Isoquinolines through IrIII-Catalyzed C-H Activation/Annulation from Benzimidates with Hydroxylisopropylalkynes
    Liu, Mingliang
    Gong, Wanchun
    You, Erli
    Zhang, Haizhen
    Shi, Lei
    Cao, Weiguo
    Shi, Jingjing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (36) : 4991 - 4995
  • [43] One-pot Synthesis of 3-Acylsilane-Substituted Isoquinolines via Rhodium (III)-Catalyzed C-H Activation/Annulation of O-pivaloyl Oximes With Acryloylsilanes
    Yang, Zengbao
    Zhou, Hui
    He, Maoyao
    Li, Jianglian
    Yang, Zhongzhen
    Wu, Yong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (07) : 1683 - 1686
  • [44] Rh-Catalyzed Ortho C-H Alkynylation of Aromatic Aldehydes
    Tan, Eric
    Nannini, Leonardo J.
    Stoica, Otilia
    Echavarren, Antonio M.
    ORGANIC LETTERS, 2021, 23 (04) : 1263 - 1268
  • [45] Rh-Catalyzed Formal [3+2] Cycloaddition Reactions with Cyclopropenones via Sequential C-H/C-C Bond Activation
    Qu, Qing-Long
    Ren, Yu-Tong
    Cao, Jun-Tao
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2025, 27 (08) : 1967 - 1972
  • [46] Rh(III)-Catalyzed Oxidative Domino C-H/N-H Annulation: Diarylureas as Arylamine Donors for the Assembly of Indolo[2,1-a]isoquinolines
    Cao, Xiyang
    Zhang, Zhiguo
    Li, Jingya
    Shi, Bingbing
    Li, Mengjuan
    Zhang, Guisheng
    Zhang, Xingjie
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21) : 13672 - 13682
  • [47] Ru(II)-Catalyzed Regioselective Annulation of 2-Hydroxystyrenes with Allenyl Acetates via Vinylic C-H Activation
    Singh, Anurag
    Shukla, Rahul K.
    Volla, Chandra M. R.
    ORGANIC LETTERS, 2022, 24 (49) : 8936 - 8941
  • [48] Rh(III)-Catalyzed Regioselective Functionalization of C-H Bonds of Naphthylcarbamates for Oxidative Annulation with Alkynes
    Zhang, Xuan
    Si, Weili
    Bao, Ming
    Asao, Naoki
    Yamamoto, Yoshinori
    Jin, Tienan
    ORGANIC LETTERS, 2014, 16 (18) : 4830 - 4833
  • [49] Rh(III)-Catalyzed C-H Activation/O-Annulation for Construction of Divergent Spirosuccinimide and Maleimide-Fused Isochromenes
    Kamaraj, Eswaran
    Roy, Prasanta
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3915 - 3926
  • [50] Cobalt(II)-Catalyzed Decarboxylative C-H Activation/Annulation Cascades: Regioselective Access to Isoquinolones and Isoindolinones
    Hao, Xin-Qi
    Du, Cong
    Zhu, Xinju
    Li, Peng-Xiang
    Zhang, Jia-Heng
    Niu, Jun-Long
    Song, Mao-Ping
    ORGANIC LETTERS, 2016, 18 (15) : 3610 - 3613