Rhodium-Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N-carbamoylindoles with Vinylene Carbonate

被引：13
作者：
Song, Jia-Lin [1 ,2 ]
Xiao, Lin [2 ]
Chen, Shao-Yong [2 ]
Zheng, Yi-Chuan [2 ]
Liu, Yan-Zhi [2 ]
Zhang, Shang-Shi [2 ]
Shu, Bing [1 ]
机构：
[1] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China
[2] Guangdong Pharmaceut Univ, Ctr Drug Res & Dev, Guangdong Prov Engn Ctr Top Precise Drug Delivery, Guangdong Prov Key Lab Adv Drug Delivery, Guangzhou 510006, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Vinylene Carbonate; Rh(III)-Catalyzed; Sulfoxonium Ylides; N-carbamoylindoles; Annulation; C-H ACTIVATION; INDOLES; CYCLIZATION; FUNCTIONALIZATION;
D O I：
10.1002/adsc.202300135
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
In this study, Rh(III)-catalyzed C-H bifunctionalization and direct vinylene annulation of sulfoxonium ylides and N-carbamoylindoles with vinylene carbonate was accomplished, which afforded a series of naphthalenones containing a beta- ketosulfoxonium ylide moiety, isocoumarins, and pyrimidones. This protocol featured mild conditions, broad substrate scope, and functional-groups compatibility. In addition, related applications and preliminary mechanistic exploratory were also investigated
引用
收藏
页码：1457 / 1464
页数：8
相关论文
共 58 条
  • [1] Cp*Co(iii)-catalyzed C-H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones
    Aher, Yogesh N.
    Pawar, Amit B.
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (58) : 7164 - 7167
  • [2] [Anonymous], 2017, ANGEW CHEM, V129, P4341
  • [3] [Anonymous], 2019, ANGEW CHEM, V131, P16344
  • [4] [Anonymous], 2017, ANGEW CHEM, V129, P13297
  • [5] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds
    Barday, Manuel
    Janot, Christopher
    Halcovitch, Nathan R.
    Muir, James
    Aissa, Christophe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13117 - 13121
  • [6] Asymmetric transformations from sulfoxonium ylides
    Caiuby, Clarice A. D.
    Furniel, Lucas G.
    Burtoloso, Antonio C. B.
    [J]. CHEMICAL SCIENCE, 2022, 13 (05) : 1192 - 1209
  • [7] Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation
    Chen, Junyu
    Zhong, Tianshuo
    Zheng, Xiangyun
    Yin, Chuanliu
    Zhang, Lei
    Zhou, Jian
    Jiang, Xinpeng
    Yu, Chuanming
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 446 - 452
  • [8] CHEN L, 2021, JOULE, V10, P2603
  • [9] Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α-Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones
    Chen, Xi
    Wang, Muhua
    Zhang, Xinying
    Fan, Xuesen
    [J]. ORGANIC LETTERS, 2019, 21 (08) : 2541 - 2545
  • [10] Rh(III)-Catalyzed [4+2] Annulation of Indoles with Diazo Compounds: Access to Pyrimido[1,6-a]indole-1(2H)-ones
    Chen, Xun
    Hu, Xinwei
    Bai, Siyi
    Deng, Yuanfu
    Jiang, Huanfeng
    Zeng, Wei
    [J]. ORGANIC LETTERS, 2016, 18 (02) : 192 - 195
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