Ruthenium(ii)-catalyzed synthesis of CF3-isoquinolinones via C-H activation/annulation of benzoic acids and CF3-imidoyl sulfoxonium ylides

被引：42
|
作者：
Wen, Si [1 ]
Zhang, Yuqing [1 ]
Tian, Qingyu [1 ]
Chen, Yanhui [1 ]
Cheng, Guolin [1 ]
机构：
[1] Huaqiao Univ, Xiamen Key Lab Optoelect Mat & Adv Mfg, Coll Mat Sci & Engn, Instrumental Anal Ctr, Xiamen 361021, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 16期
关键词：
REGIOSELECTIVE SYNTHESIS; ACTIVATION; BENZAMIDES; ANNULATION; FLUORINE; ALKYNES; BOND; COUPLING/CYCLIZATION; ISOQUINOLINONES; CYCLIZATION;
D O I：
10.1039/d2qo00839d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ruthenium(ii)-catalyzed C-H activation/annulation reaction of benzoic acids and CF3-imidoyl sulfoxonium ylides enabled by weak O-coordination has been achieved. A series of 3-trifluoromethylisoquinolinones were synthesized in 37-75% yields under redox-neutral reaction conditions.
引用
收藏
页码：4388 / 4393
页数：6
相关论文
共 50 条
  • [31] One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols
    Pan, Mingshi
    Tong, Yixin
    Qiu, Xiaodong
    Zeng, Xiaobao
    Xiong, Biao
    CHEMICAL COMMUNICATIONS, 2022, 58 (89) : 12443 - 12446
  • [32] Ruthenium(II)-catalyzed N-substituted phthalimide synthesis via C-H activation/[3+2] annulation
    Dong, Xue-Fen
    Fan, Juan
    Shi, Xian-Ying
    Liu, Ke-Yan
    Wang, Peng-Min
    Wei, Jun-Fa
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 779 : 55 - 61
  • [33] Ruthenium(ii)-catalyzed selective C-H bond activation of imidamides and coupling with sulfoxonium ylides: an efficient approach for the synthesis of highly functional 3-ketoindoles
    Wu, Chenglin
    Zhou, Jianhui
    He, Guoxue
    Li, Huihui
    Yang, Qiaolan
    Wang, Run
    Zhou, Yu
    Liu, Hong
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (08) : 1183 - 1188
  • [34] Rhodium(iii)-catalyzed regioselective C2-alkenylation of indoles with CF3-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group
    Yang, Zuguang
    Tang, Jianhua
    Li, Chen
    Chen, Zhengkai
    Wu, Xiao-Feng
    CHEMICAL COMMUNICATIONS, 2023, 59 (03) : 318 - 321
  • [35] Synthesis of 5-Trifluoromethyl-1,4-dihydro-1,2,4-triazines via Base-mediated [3+3] Cycloaddition of Nitrile Imines and CF3-Imidoyl Sulfoxonium Ylides
    Sun, Yue
    Ling, Sihao
    Duan, Yubo
    Li, Jingxian
    Chen, Zhengkai
    Wu, Xiao-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) : 1521 - 1525
  • [36] Synthesis of 2-Trifluoromethyl-4-aminoquinolines via Heating-Promoted Multi-component Reaction of CF3-Imidoyl Sulfoxonium Ylides and Amines with Difluorocarbene as a C1 Synthon
    Wei, Guangming
    Li, Chen
    Wang, Haoyuan
    Chen, Zhengkai
    Wu, Xiao-Feng
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (23) : 3205 - 3210
  • [37] Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
    Song, Xiaohan
    Han, Xu
    Zhang, Rui
    Liu, Hong
    Wang, Jiang
    MOLECULES, 2019, 24 (10):
  • [38] Ruthenium-catalyzed coupling of α-carbonyl phosphoniums with sulfoxonium ylides via C-H activation/Wittig reaction sequences
    Chen, Tian
    Ding, Zhiqiang
    Guan, Yuqiu
    Zhang, Ruike
    Yao, Jinzhong
    Chen, Zhangpei
    CHEMICAL COMMUNICATIONS, 2021, 57 (21) : 2665 - 2668
  • [39] Synthesis of CF3-Containing Spiro-[Indene-Proline] Derivatives via Rh(III)-Catalyzed C-H Activation/Annulation
    Bubnova, Alexandra S.
    Vorobyeva, Daria V.
    Godovikov, Ivan A.
    Smol'yakov, Alexander F.
    Osipov, Sergey N.
    MOLECULES, 2023, 28 (23):
  • [40] Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides via C-C bond activation
    Wen, Si
    Lv, Weiwei
    Ba, Dan
    Liu, Jing
    Cheng, Guolin
    CHEMICAL SCIENCE, 2019, 10 (39) : 9104 - 9108
12345