Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines

被引：35
|
作者：
Chen, Renjie [1 ]
Qi, Jifeng [1 ]
Mao, Zhenjun [1 ]
Cui, Sunliang [1 ]
机构：
[1] Zhejiang Univ, Inst Drug Discovery & Design, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 26期
基金：
中国国家自然科学基金;
关键词：
N BOND FORMATION; BETA-PHENYLETHYLAMINES; INTERNAL ALKYNES; FACILE SYNTHESIS; ACTIVATION; ACCESS; ACIDS; ANNULATION; BENZAMIDES; ALKALOIDS;
D O I：
10.1039/c6ob00942e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Rh(III)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine. A kinetic isotope effect study was conducted and a plausible mechanism was proposed.
引用
收藏
页码：6201 / 6204
页数：4
相关论文
共 50 条
  • [41] Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation
    Jiang, Yuqin
    Li, Pengfei
    Zhao, Jie
    Liu, Bingxian
    Li, Xingwei
    ORGANIC LETTERS, 2020, 22 (19) : 7475 - 7479
  • [42] Rh(III)-Catalyzed Regioselective Alkyne Insertion in the Context of C-H Activation and Lactonization Reactions: Synthesis of Fused 1,2-Oxaphospholenes
    Yang, Yingying
    Chen, Menghan
    Xuan, Qingqing
    Xu, Jian
    Song, Qiuling
    ORGANIC LETTERS, 2024, 26 (36) : 7683 - 7687
  • [43] Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
    Xu, Shiyang
    Huang, Baoliang
    Qiao, Guanyu
    Huang, Ziyue
    Zhang, Zhen
    Li, Zongyang
    Wang, Peng
    Zhang, Zhenhua
    ORGANIC LETTERS, 2018, 20 (18) : 5578 - 5582
  • [44] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
    Hou, Xinjiao
    Wang, Run
    Fang, Feifei
    Qu, Zhiyan
    Zhou, Jianhui
    Yu, Ting
    Wang, Dechuan
    Liu, Hong
    Zhou, Yu
    ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
  • [45] 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
    ORGANIC LETTERS, 2014, 16 (02) : 330 - 333
  • [46] Rh(iii)-catalyzed [4+1] cyclization of aryl substituted pyrazoles with cyclopropanols via C-H activation
    Chen, Wenxi
    Mao, Yan
    Wang, Min
    Ling, Fei
    Li, Changchang
    Chen, Zhangpei
    Yao, Jinzhong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (04) : 775 - 782
  • [47] Synthesis of 4-Cyclobutene-Isoquinolines From Aryl Imidates by Ru(II)-Catalyzed Domino C-H Activation/Cyclization
    Wang, Min
    Gao, Lei
    Miao, Maozhong
    Zong, Qianshou
    Ling, Fei
    Yao, Jinzhong
    Zhou, Hongwei
    APPLIED ORGANOMETALLIC CHEMISTRY, 2025, 39 (03)
  • [48] From Indoles to Carbazoles: Tandem Cp*Rh(III)-Catalyzed C-H Activation/Bronsted Acid-Catalyzed Cyclization Reactions
    Wu, Jia-Qiang
    Yang, Zhen
    Zhang, Shang-Shi
    Jiang, Chun-Yong
    Li, Qingjiang
    Huang, Zhi-Shu
    Wang, Honggen
    ACS CATALYSIS, 2015, 5 (11): : 6453 - 6457
  • [49] Theoretical studies on Rh(III)-catalyzed regioselective C-H bond cyanation of indole and indoline
    Deng, Chao
    Sun, Yingxin
    Ren, Yi
    Zhang, Weihua
    DALTON TRANSACTIONS, 2019, 48 (01) : 168 - 175
  • [50] Rh(iii)-Catalyzed allylic C-H amidation of unactivated alkenes with in situ generated iminoiodinanes
    Sihag, Pinki
    Jeganmohan, Masilamani
    CHEMICAL COMMUNICATIONS, 2021, 57 (52) : 6428 - 6431
12345