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
  • [21] Ruthenium(II)-Catalyzed Construction of Isocoumarins via Dual C-H/C-C Activation of Sulfoxonium Ylides
    Wen, Si
    Chen, Yanhui
    Zhao, Zemin
    Ba, Dan
    Lv, Weiwei
    Cheng, Guolin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 1216 - 1223
  • [22] Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides
    Xu, Youwei
    Yang, Xifa
    Zhou, Xukai
    Kong, Lingheng
    Li, Xingwei
    ORGANIC LETTERS, 2017, 19 (16) : 4307 - 4310
  • [23] Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides
    Zhang, Jin
    Wang, Xiaogang
    Chen, Di
    Kang, Yifan
    Ma, Yangmin
    Szostak, Michal
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3192 - 3201
  • [24] Rh(III) Catalyzed Redox-Neutral C-H Activation/[5+2] Annulation of Aroyl Hydrazides and Sulfoxonium Ylides: Synthesis of Benzodiazepinones
    Ganesh, PothapragadaS. K. Prabhakar
    Muthuraja, Perumal
    Gopinath, Purushothaman
    ORGANIC LETTERS, 2023, 25 (46) : 8361 - 8366
  • [25] Rh(III)-Catalyzed C-H Annulation of Sulfoxonium Ylides and 1,3-Diynes: A Rapid Access to Alkynyl-1-Naphthol Derivatives
    Kumar, Sanjeev
    Borkar, Vaishnavi
    Nunewar, Saiprasad
    Yadav, Shashank
    Kanchupalli, Vinaykumar
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (08)
  • [26] Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C-H Functionalization of Sulfoxonium Ylides with 1,3-Diynes
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Sabbi, Tharun Kumar
    Kanchupalli, Vinaykumar
    ORGANIC LETTERS, 2022, 24 (18) : 3395 - 3400
  • [27] Maleimide-Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)-Catalyzed C-H Activation of Sulfoxonium Ylides
    Muthuraja, Perumal
    Akhtar, Muhammad Saeed
    Gopinath, Purushothaman
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4595 - 4602
  • [28] Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium-Catalyzed Synthesis of Phenanthrenes
    Liu, Xiao
    Zhou, Bingxin
    Yan, Kelu
    Wen, Jiangwei
    Li, Qiuyun
    Wang, Xutong
    Wang, Xiu
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (08) : 1744 - 1750
  • [29] Rhodium(iii)-catalyzed annulation of enamides with sulfoxonium ylides toward isoquinolines
    Hong, Chao
    Yu, Shuling
    Liu, Zhanxiang
    Zhang, Yuhong
    RSC ADVANCES, 2021, 11 (19) : 11490 - 11494
  • [30] Rh(III)-Catalyzed C-H Cyclization of Primary Benzylamines with Iodonium Ylides toward Dihydrophenanthridin-1-ones
    Zhai, Ruirui
    Jiao, Liulin
    Qu, Bohong
    Yang, Xiaoping
    Chen, Xun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (11)
12345