Ruthenium(II)-Catalyzed Remote C-H Sulfonylation of 2-Pyridones

被引：8
|
作者：
Yang, Fengqi [1 ]
Zhou, Pengfei [1 ]
Huang, Zeng [1 ]
Liao, Junqiu [1 ]
Huang, Guan [1 ]
Liang, Taoyuan [1 ]
Zhang, Zhuan [1 ]
机构：
[1] Guangxi Univ, Sch Chem & Chem Engn, Guangxi Coll & Univ Key Lab Appl Chem Technol & Re, Guangxi Key Lab Electrochem Energy Mat, Nanning 530004, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 31期
关键词：
DIRECT ALKYLATION; FUNCTIONALIZATION; ARYLATION; SULFONES; ALKYNYLATION; HETEROCYCLES; DERIVATIVES;
D O I：
10.1021/acs.orglett.3c02004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, a ruthenium-mediated remoteC-H mono- and disulfonylationof 2-pyridones with arylsulfonyl chlorides is developed. The catalyticsystem consisting of a [Ru(p-cymene)Cl-2](2) catalyst and KOAc additive allows 2-pyridones to undergoC3,C5-disulfonylation in 1,4-dioxane, and C5-sulfonylation when theC3-position of 2-pyridones is blocked. The successful transformationof the products and late-stage modification of estrone further highlightedthe potential utility and significance of this synthetic protocol.Preliminary mechanistic studies indicated that the remote regioselectivitymight be dictated via chelation-assisted ruthenation.
引用
收藏
页码：5779 / 5783
页数：5
相关论文
共 50 条
  • [1] Ru(ii)-Catalyzed C6-selective C-H amidation of 2-pyridones
    Zhang, Lei
    Zheng, Xiangyun
    Chen, Jinkang
    Cheng, Kang
    Jin, Licheng
    Jiang, Xinpeng
    Yu, Chuanming
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2969 - 2973
  • [2] Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations
    Ackermann, Lutz
    Lygin, Alexander V.
    Hofmann, Nora
    ORGANIC LETTERS, 2011, 13 (12) : 3278 - 3281
  • [3] Ruthenium-catalyzed site-selective C-H arylation of 2-pyridones and 1-isoquinolinones
    Kumar, K. Anil
    Kannaboina, Prakash
    Das, Parthasarathi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (26) : 5457 - 5461
  • [4] Co(III) or Ru(II)-Catalyzed Selective C-H Alkynylation of 2-Pyridones and Their Derivatives with Bromoalkynes
    Luo, Quanjian
    Wang, Hanchi
    Zhou, Jierui
    Wang, Siyuan
    Li, Jinheng
    Sun, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [5] Cu(II)-catalyzed C6-selective C-H thiolation of 2-pyridones using air as the oxidant
    Peng, Panfeng
    Wang, Jiang
    Li, Chunpu
    Zhu, Wei
    Jiang, Hualiang
    Liu, Hong
    RSC ADVANCES, 2016, 6 (62) : S7441 - S7445
  • [6] Rhodium-Catalyzed C6-Selective C-H Borylation of 2-Pyridones
    Miura, Wataru
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2016, 18 (15) : 3742 - 3745
  • [7] Iridium-Catalyzed Site-Selective C-H Borylation of 2-Pyridones
    Miura, Wataru
    Hirano, Koji
    Miura, Masahiro
    SYNTHESIS-STUTTGART, 2017, 49 (21): : 4745 - 4752
  • [8] Palladium-Catalyzed C6-Selective C-H Acylation of 2-Pyridones
    Chen, Zhiwei
    Zhang, Lei
    Zhao, Danxia
    Hu, Gangao
    Yu, Chuanming
    SYNLETT, 2021, 32 (03) : 299 - 303
  • [9] RhIII-Catalyzed C6-Selective Oxidative C-H/C-H Crosscoupling of 2-Pyridones with Thiophenes
    Huang, Gao
    Shan, Yujia
    Yu, Jin-Tao
    Pan, Changduo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (48) : 12294 - 12299
  • [10] Rhodium(III)-Catalyzed Regioselective C-H Annulation and Alkenylation of 2-Pyridones with Terminal Alkynes
    Li, Jiajie
    Xu, Xin
    Luo, Zhenli
    Yao, Zhen
    Yang, Ji
    Zhang, Xin
    Xu, Lijin
    Wang, Peng
    Shi, Qian
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (07) : 1264 - 1270
12345