Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C-H/N-O bond activation

被引：13
|
作者：
Lin, Wei [1 ]
Hu, Xiu-Xiu [1 ]
Zhuang, Cang-Wei [1 ]
Wang, Ya-Zhen [1 ]
机构：
[1] Jiangsu Univ Technol, Sch Chem & Environm Engn, Changzhou 213001, Peoples R China
来源：
TETRAHEDRON | 2019年 / 75卷 / 22期
关键词：
Isoquinoline; Synthesis; Cyclization; Iridium(III)-catalysis; H FUNCTIONALIZATION; BETA-PHENYLETHYLAMINES; DIRECTING GROUPS; 4+2 ANNULATION; N-OXIDE; AMIDATION; OXIMES; ALKYNYLATION; HETEROCYCLES; CYCLIZATION;
D O I：
10.1016/j.tet.2019.04.039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient approach to synthesize isoquinoline derivatives through Iridium(III)-catalyzed cyclization of aryl ketoximes and internal alkynes without oxidant is reported. A broad range isoquinolines are obtained in good to excellent yields and various functional groups are well tolerated. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3015 / 3023
页数：9
相关论文
共 50 条
  • [31] Synthesis of Benzofulvenes via Cp*Co(III)-Catalyzed C-H Activation and Carbocyclization of Aromatic Ketones with Internal Alkynes
    Yu, Yongqi
    Wu, Qianlong
    Liu, Da
    Hu, Liang
    Yu, Lin
    Tan, Ze
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 7449 - 7458
  • [32] A removable directing group-assisted Rh(iii)-catalyzed direct C-H bond activation/annulation cascade to synthesize highly fused isoquinolines
    Cheng, Yilang
    Han, Xu
    Li, Junyou
    Zhou, Yu
    Liu, Hong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (20): : 3186 - 3192
  • [33] Rhodium-catalyzed oxidative coupling of 2-aryl-imidazopyridines with internal alkynes via double C-H activation
    Kotla, Siva
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [34] Cationic iridium-BINAP complex-catalyzed addition of aryl ketones to alkynes and alkenes via directed C-H bond cleavage
    Tsuchikama, Kyoji
    Kasagawa, Mitsugu
    Hashimoto, Yu-Ki
    Endo, Kohei
    Shibata, Takanori
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (26) : 3939 - 3942
  • [35] Rhodium(III)-catalyzed cascade oxidative annulation reactions of aryl imidazolium salts with alkynes involving multiple C-H bond activation
    Ge, Qingmei
    Li, Bin
    Song, Haibin
    Wang, Baiquan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) : 7695 - 7710
  • [36] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [37] Theoretical Investigations on Rh(III)-Catalyzed Cross-Dehydrogenative Aryl-Aryl Coupling via C-H Bond Activation
    Zhao, Dan
    Li, Xiaoxi
    Han, Keli
    Li, Xingwei
    Wang, Yong
    JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (12): : 2989 - 2997
  • [38] Selective Synthesis of Indoles by Cobalt(III)-Catalyzed C-H/N-O Functionalization with Nitrones
    Wang, Hui
    Moselage, Marc
    Gonzalez, Maria J.
    Ackermann, Lutz
    ACS CATALYSIS, 2016, 6 (04): : 2705 - 2709
  • [39] Cp*Co(III) catalyzed annulation of N-Cbz hydrazones for the redox-neutral synthesis of isoquinolines via C-H/N-N bond activation
    Subhedar, Dnyaneshwar D.
    Deshmukh, Dewal S.
    Bhanage, Bhalchandra M.
    SYNTHETIC COMMUNICATIONS, 2019, 49 (22) : 3121 - 3130
  • [40] N-O Bond as External Oxidant in Group 9 Cp*M(III)-Catalyzed Oxidative C-H Coupling Reactions
    Liu, Xu-Ge
    Gao, Hui
    Zhang, Shang-Shi
    Li, Qingjiang
    Wang, Honggen
    ACS CATALYSIS, 2017, 7 (08): : 5078 - 5086
12345