Copper-catalyzed visible-light-induced ring-opening carbonylation of sulfonium salts

被引:9
|
作者
Zhang, Youcan [1 ]
Bao, Zhi-Peng [1 ,2 ]
Kuai, Chang-Sheng [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Liaoning, Peoples R China
[2] Leibniz Inst Katalyse e V, Albert Einstein Str 29a, D-18059 Rostock, Germany
基金
中国博士后科学基金;
关键词
Visible light; Copper catalysis; Carbonylation; Sulfonium salts; Radical reaction;
D O I
10.1016/j.jcat.2023.06.039
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Herein, we developed a direct and effective strategy for the synthesis of sulfur-containing carboxylic acid derivatives through copper/visible light catalyzed ring-opening carbonylation of sulfonium salts. The pro-tocol employs photoredox to promote the selective cleavage of sulfonium salts C(sp3)-S bond, while per-forming sequential functionalization to form vicinal C-C and C-X (X = O or N) bonds in the presence of carbon monoxide and nucleophiles. A variety of substrates were successfully transformed into the desired carbonylated products in moderate to good yields with good functional group tolerance and excellent chemoselectivity. Importantly, this approach can be easily extended to late-stage modification of bioactive molecules. & COPY; 2023 Elsevier Inc. All rights reserved.
引用
收藏
页码:1 / 5
页数:5
相关论文
共 50 条
  • [1] Visible-Light-Induced Radical Type Ring-Opening of Sulfonium Salts with Heteroarenes by Copper Photocatalyst
    Zhu, Xiaolong
    Song, Xiuyan
    Li, Xuan
    Wang, Fengxiao
    Lv, Jian
    Jiang, Min
    Yang, Daoshan
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4384 - 4391
  • [2] Anti-Markovnikov Ring-Opening of Sulfonium Salts with Alkynes Catalyzed by Visible Light/Copper
    Yi, Rongnan
    He, Weimin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (08) : 2985 - 2987
  • [3] Anti-Markovnikov ring-opening of sulfonium salts with alkynes by visible light/copper catalysis
    Xuan Li
    Min Jiang
    Junze Zuo
    Xiuyan Song
    Jian Lv
    Daoshan Yang
    Science China Chemistry, 2023, 66 (03) : 791 - 798
  • [4] Anti-Markovnikov ring-opening of sulfonium salts with alkynes by visible light/copper catalysis
    Xuan Li
    Min Jiang
    Junze Zuo
    Xiuyan Song
    Jian Lv
    Daoshan Yang
    Science China Chemistry, 2023, 66 : 791 - 798
  • [5] Anti-Markovnikov ring-opening of sulfonium salts with alkynes by visible light/copper catalysis
    Li, Xuan
    Jiang, Min
    Zuo, Junze
    Song, Xiuyan
    Lv, Jian
    Yang, Daoshan
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (03) : 791 - 798
  • [6] Visible-Light-Induced Copper-Catalyzed Alkynylation/Alkylation of Alkenes
    Zhang, Yajing
    Zhang, Dayong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3213 - 3223
  • [7] Copper-Catalyzed Ring-Opening/Borylation of Cyclopropenes
    Huang, Ming-Yao
    Zhao, Yu-Tao
    Chai, Hao
    Zhang, Cheng-Da
    Zhu, Shou-Fei
    CCS CHEMISTRY, 2022, 4 (04): : 1232 - 1237
  • [8] Radial Type Ring Opening of Sulfonium Salts with Dichalcogenides by Visible Light and Copper Catalysis
    Cui, Wenwen
    Li, Xufeng
    Guo, Guoju
    Song, Xiuyan
    Lv, Jian
    Yang, Daoshan
    ORGANIC LETTERS, 2022, 24 (29) : 5391 - 5396
  • [9] Copper-Catalyzed Asymmetric Ring-Opening Reaction of Cyclic Diaryliodonium Salts with Imides
    Cheng, Fu
    Duan, Dong-Sen
    Jiang, Li-Ming
    Li, Bao-Sheng
    Wang, Jia-Xuan
    Zhou, Yu-Jia
    Jiao, He-Yu
    Wu, Tao
    Zhu, Dao-Yong
    Wang, Shao-Hua
    ORGANIC LETTERS, 2022, 24 (06) : 1394 - 1399
  • [10] Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes
    Xiong, Yang
    Zhang, Guozhu
    ORGANIC LETTERS, 2019, 21 (19) : 7873 - 7877