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
  • [11] Formal Gold- and Rhodium-Catalyzed Regiodivergent C-H Alkynylation of 2-Pyridones
    Li, Yunyun
    Xie, Fang
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02): : 715 - 722
  • [12] CpIr-Catalyzed C-H Arylation of 2-Pyridones and 1-Isoquinolinones with Arylsilanes
    Su, Tongxu
    Xu, Heng
    Dong, Yi
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (09) : 2109 - 2114
  • [13] Ruthenium-Catalyzed Remote C-H Sulfonylation of N-Aryl-2-aminopyridines with Aromatic Sulfonyl Chlorides
    Ramesh, Balu
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2017, 19 (21) : 6000 - 6003
  • [14] Regioselective Functionalization of 2-Pyridones through C-H Bond Activation
    Matsubara, Tatsuaki
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (07) : 753 - 754
  • [15] Manganese Catalyzed Site-Selective Hydroxymethylation to 2-Pyridones and Isoquinolones via C-H Activation
    Rastogi, Anushka
    Kumar, Mohit
    Gangwar, Manoj Kumar
    Koley, Dipankar
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (18) : 3815 - 3821
  • [16] Ruthenium(II)-catalyzed C-H activation
    Ackermann, Lutz
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [17] Co(III)-Catalyzed C6-Selective C-H Activation/Pyridine Migration of 2-Pyridones with Propiolates
    Zhu, Yue-Lu
    Zhao, Na
    Fu, Xin-Long
    Zhao, Xin-Yang
    Li, Yan-Lin
    Shao, You-Dong
    Chen, Jiao
    Lu, Yi
    ORGANIC LETTERS, 2023, 26 (01) : 12 - 17
  • [18] PYRIDINE-DIRECTED Rh-CATALYZED C6-SELECTIVE C-H ACETOXYLATION OF 2-PYRIDONES
    Hazra, Sunit
    Hirano, Koji
    Miura, Masahiro
    HETEROCYCLES, 2020, 101 (01) : 223 - 234
  • [19] An efficient method for the synthesis of 2-pyridones via C-H bond functionalization
    Zhou, Shuguang
    Liu, Duan-Yang
    Wang, Suo
    Tian, Jie-Sheng
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2020, 56 (95) : 15020 - 15023
  • [20] Ruthenium(II)-Catalyzed C-H Chalcogenation of Anilides
    Ma, Wenbo
    Weng, Zhengyun
    Rogge, Torben
    Gu, Linghui
    Lin, Jiafu
    Peng, Ai
    Luo, Xiang
    Gou, Xiaojun
    Ackermann, Lutz
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 704 - 710
12345