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
  • [21] Visible-Light-Induced Copper-Catalyzed Intermolecular Three-Component Difluoroalkyl Thiocyanidation of Alkenes
    Hu, Zhaoming
    Wang, Yanzhao
    Wang, Kaiji
    Wu, Jingjing
    Wu, Fanhong
    ORGANIC LETTERS, 2023, 25 (26) : 4835 - 4839
  • [22] Copper-Catalyzed Visible-Light-Induced Allylic Difluoromethylation of Unactivated Alkenes Using Difluoroacetic Acid
    Wang, Jinlian
    Luo, Ziwei
    Wu, Yili
    Tang, Yihan
    Yang, Xinkan
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2023, 25 (06) : 1045 - 1049
  • [23] Visible-Light-Induced Palladium-Catalyzed Dehydrogenative Carbonylation of Amines to Oxalamides
    Meyer, Tim
    Rabeah, Jabor
    Brueckner, Angelika
    Wu, Xiao-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (18) : 5642 - 5647
  • [24] Visible-Light-Induced Decarboxylative Alkylation/Ring Opening and Esterification of Vinylcyclopropanes
    Chen, Pu
    Huang, Peng-Fei
    Xiong, Bi-Quan
    Huang, Hua-Wen
    Tang, Ke-Wen
    Liu, Yu
    ORGANIC LETTERS, 2022, 24 (31) : 5726 - 5730
  • [25] Development of a Robust Procedure for the Copper-catalyzed Ring-Opening of Epoxides with Grignard Reagents
    Alam, Mahbub
    Wise, Christopher
    Baxter, Carl A.
    Cleator, Ed
    Walkinshaw, Andrew
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (03) : 435 - 441
  • [26] Copper-Catalyzed Enantioselective Ring-Opening of Cyclic Diaryliodoniums and O-Alkylhydroxylamines
    Li, Qigang
    Zhang, Mingkai
    Zhan, Shuming
    Gu, Zhenhua
    ORGANIC LETTERS, 2019, 21 (16) : 6374 - 6377
  • [27] UNUSUAL STEREOCHEMISTRY IN THE COPPER-CATALYZED RING-OPENING OF A CARBOHYDRATE OXIRANE WITH VINYLMAGNESIUM BROMIDE
    BROCKWAY, C
    KOCIENSKI, P
    PANT, C
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05): : 875 - 878
  • [28] Insights into the Mechanism of Enantioselective Copper-Catalyzed Ring-Opening Allylic Alkylation of Cyclopropanols
    Kitabayashi, Akito
    Mizushima, Sho
    Higashida, Kosuke
    Yasuda, Yuto
    Shimizu, Yohei
    Sawamura, Masaya
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (11) : 1855 - 1862
  • [29] Enantioselective Copper-Catalyzed Radical Ring-Opening Cyanation of Cyclopropanols and Cyclopropanone Acetals
    Wu, Lianqian
    Wang, Lei
    Chen, Pinghong
    Guo, Yin-Long
    Liu, Guosheng
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (11) : 2189 - 2194
  • [30] Copper-Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Grignard and Aluminum Reagents
    Millet, Renaud
    Gremaud, Ludovic
    Bernardez, Tania
    Palais, Laetitia
    Alexakis, Alexandre
    SYNTHESIS-STUTTGART, 2009, (12): : 2101 - 2112