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
  • [41] Copper-Catalyzed Remote C-H Sulfonylation of 8-Aminoquinoline Amides with Arylsulfonyl Hydrazides
    Chen, Guoshu
    Zhang, Xuejian
    Zeng, Zihui
    Peng, Wanying
    Liang, Qiongzhi
    Liu, Jidan
    CHEMISTRYSELECT, 2017, 2 (05): : 1979 - 1982
  • [42] Electrolyte-free electrochemical C-H trifluoromethylation of 2-pyridones under batch and flow conditions
    Leclercq, Elise
    Moncomble, Aurelien
    Debavelaere, Celine
    Beaucamp, Mathieu
    Penhoat, Mael
    Chausset-Boissarie, Laetitia
    GREEN CHEMISTRY, 2022, 24 (19) : 7388 - 7394
  • [43] Site-Selective C-H Arylation of 2-Pyridones via Pd/NBE Cooperative Catalysis
    Sun, Ziyi
    Jiang, Zibin
    He, Fengya
    Li, Chenyue
    Xiong, Hujie
    Yang, Dan
    Miao, Hui
    Li, Qinglin
    Ye, Jinxiang
    Wu, Chenggui
    ACS CATALYSIS, 2024, 14 (10): : 7762 - 7770
  • [44] Ruthenium(II)-Catalyzed Hydrogen Isotope Exchange of Pharmaceutical Drugs by C-H Deuteration and C-H Tritiation
    Mueller, Valentin
    Weck, Remo
    Derdau, Volker
    Ackermann, Lutz
    CHEMCATCHEM, 2020, 12 (01) : 100 - 104
  • [45] Ruthenium(II)-Catalyzed C-H/C-H (4+2) Annulation of 2-Aryl-N-heterocycles with Vinylene Carbonate
    Nipate, Dhananjay S.
    Swami, Prakash N.
    Gadekar, Amol B.
    Jangir, Tarun
    Rangan, Krishnan
    Kumar, Anil
    CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (03)
  • [46] Remote C-H Functionalizations by Ruthenium Catalysis
    Ackermann, Lutz
    Samanta, Ramesh C.
    Rogge, Torben
    Ackermann, Lutz
    SYNTHESIS-STUTTGART, 2021, 53 (17): : 2911 - 2934
  • [47] Ruthenium(II)-Catalyzed S(II)-Directed Aromatic C-H Allylation with Vinylaziridines
    Duan, Yu-Tong
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23): : 16076 - 16090
  • [48] Rhodium(III)-Catalyzed C-H Bond Functionalization of 2-Pyridones with Alkynes: Switchable Alkenylation, Alkenylation/Directing Group Migration and Rollover Annulation
    Xu, Xin
    Luo, Chenguang
    Zhao, Haoqiang
    Pan, Yixiao
    Zhang, Xin
    Li, Jiajie
    Xu, Lijin
    Lei, Ming
    Walsh, Patrick J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (34) : 8811 - 8821
  • [49] Ruthenium-Catalyzed PIII-Directed Remote ε-C-H Alkylation of Phosphines
    Xu, Hui-Bei
    Chen, Yin-Jun
    Chai, Xin-Yue
    Yang, Jia-Hui
    Xu, Yan-Jun
    Dong, Lin
    ORGANIC LETTERS, 2021, 23 (06) : 2052 - 2056
  • [50] Ruthenium(II)-Catalyzed Direct C-H Arylation of Indoles with Arylsilanes in Water
    Nareddy, Pradeep
    Jordan, Frank
    Szostak, Michal
    ORGANIC LETTERS, 2018, 20 (02) : 341 - 344
12345