Rh(iii)-catalyzed C-H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins

被引：31
|
作者：
Yin, Chuanliu [1 ]
Li, Lianghao [1 ]
Yu, Chuanming [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 05期
基金：
中国国家自然科学基金;
关键词：
HYDRANGEAE-DULCIS FOLIUM; CYCLIZATION; ANTIFUNGAL; ACTIVATION; STRATEGIES; CARBENES; INDOLES; ACCESS;
D O I：
10.1039/d1ob02273c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The direct synthesis of isocoumarin skeletons has been realized through the Rh(iii)-catalyzed [3 + 3] annulation of sulfoxonium ylides with iodonium carbenes. The synthetic protocol was constructed efficiently with broad functional group tolerance and mild reaction conditions. This reaction can be formally viewed as the result of C-H activation, carbene insertion and nucleophilic addition processes. Furthermore, the further conversions of the product and gram-scale reactions were also demonstrate to support the effectiveness of the synthesis protocol.
引用
收藏
页码：1112 / 1116
页数：5
相关论文
共 50 条
  • [41] Synthesis of 1-aminoindole derivatives via Rh(iii)-catalyzed annulation reactions of hydrazines with sulfoxonium ylides
    Xie, Wucheng
    Chen, Xin
    Shi, Junjun
    Li, Jieshen
    Liu, Riyao
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15) : 2662 - 2666
  • [42] 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):
  • [43] Synthesis of CF3-Indazoles via Rh(III)-Catalyzed C-H [4+1] Annulation of Azobenzenes with CF3-Imidoyl Sulfoxonium Ylides
    Shang, Yilong
    Li, Chen
    Wang, Guiqiu
    Yao, Guiwei
    Wu, Hongliang
    Chen, Xun
    Zhai, Ruirui
    MOLECULES, 2025, 30 (01):
  • [44] Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C-H Activation/Cyclopropanation Cascade
    Lou, Jiang
    Wang, Quannan
    Zhou, Yong-Gui
    Yu, Zhengkun
    ORGANIC LETTERS, 2019, 21 (22) : 9217 - 9222
  • [45] Rh(III)-Catalyzed C-H Cyclization of 2-Arylbenzimidazoles with CF3-Imidoyl Sulfoxonium Ylides and Further Sc(III)-Catalyzed Deaminative Hydroxylation
    Liao, Juting
    Zhai, Ruirui
    Gao, Xiaoyang
    Wu, Hongliang
    Kong, Dulin
    Wang, Shuojin
    Chen, Xun
    ADVANCED SYNTHESIS & CATALYSIS, 2024,
  • [46] Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides
    Zhu, Shuai
    Shi, Kai
    Zhu, Hao
    Jia, Zhe-Kang
    Xia, Xiao-Feng
    Wang, Dawei
    Zou, Liang-Hua
    ORGANIC LETTERS, 2020, 22 (04) : 1504 - 1509
  • [47] Electrochemical promoted C-H bond chlorination of sulfoxonium ylides
    Zhang, Li -Ming
    Fu, Zi-Hao
    Yuan, Da-Fu
    Guo, Ming-Zhong
    Li, Ming
    Wen, Li-Rong
    Zhang, Lin-Bao
    TETRAHEDRON LETTERS, 2023, 114
  • [48] Ir(III)-catalyzed C-H alkenylation/annulation of N-iminopyridinium ylides with acrylates and alkynes
    Chen, Xiaopei
    Ma, Zhiwei
    Wang, Chuanchuan
    Hou, Xuehui
    Liu, Juntao
    TETRAHEDRON, 2024, 168
  • [49] Rh(iii)-catalyzed C-H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones
    Duan, Yubo
    Lu, Shu-Ning
    Yang, Zuguang
    Chen, Zhengkai
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (15) : 3843 - 3848
  • [50] Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C-H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides
    Ma, Wenbo
    Tan, Yuqiang
    Wang, Yang
    Li, Zhiyi
    Li, Zheyu
    Gu, Linghui
    Mei, Ruhuai
    Cheng, An
    ORGANIC LETTERS, 2021, 23 (16) : 6200 - 6205
12345