Visible-Light Copper Catalysis for the Synthesis of α-Alkyl- Acetophenones by the Radical-Type Ring Opening of Sulfonium Salts and Oxidative Alkylation of Alkenes

被引:21
作者
Li, Xuan [1 ]
Li, Xufeng [2 ]
Cui, Wenwen [1 ]
Wu, Qilong [1 ]
Wang, Linyuan [1 ]
Lv, Jian [1 ]
Yang, Daoshan [1 ,3 ]
机构
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, MOE, Key Lab Opt Elect Sensing & Analyt Chem Life Sci, Qingdao 266042, Peoples R China
[2] Zhejiang Wansheng Co Ltd, Linhai 317000, Zhejiang, Peoples R China
[3] Nanjing Forestry Univ, Natl Engn Res Ctr Low Carbon Proc & Utilizat Fores, Nanjing 210037, Peoples R China
基金
中国国家自然科学基金;
关键词
PHOTOREDOX CATALYSIS; ARYL IODIDES; KETONES; FUNCTIONALIZATION; VINYLARENES; GENERATION; ARYLATION; OLEFINS;
D O I
10.1021/acs.orglett.3c00990
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct difunctionalization of simple alkenes has been treated as a powerful synthetic strategy for the construction of highly functionalized skeletons. In this study, direct oxidative coupling of sulfonium salts with alkenes was achieved under mild conditions by a blue-light-driven photoredox process using a copper complex as a photosensitizer. This protocol allows regioselective synthesis of aryl/alkyl ketones from simple sulfonium salts and aromatic alkenes via selective C-S bond cleavage of sulfonium salts and oxidative alkylation of aromatic alkenes using dimethyl sulfoxide (DMSO) as a mild oxidant.
引用
收藏
页码:3260 / 3265
页数:6
相关论文
共 61 条
  • [21] Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst
    Han, Bowen
    Li, Yanjun
    Yu, Ying
    Gong, Lei
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)
  • [22] A photoredox catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of oxime esters and styrenes: synthesis of ketonitriles
    He, Bin-Qing
    Yu, Xiao-Ye
    Wang, Peng-Zi
    Chen, Jia-Rong
    Xiao, Wen-Jing
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (86) : 12262 - 12265
  • [23] Visible-light-promoted oxidative decarboxylation of arylacetic acids in air: Metal-free synthesis of aldehydes and ketones at room temperature
    He, Shuaiqi
    Chen, Xiaolan
    Zeng, Fanlin
    Lu, Peipei
    Peng, Yuyu
    Qu, Lingbo
    Yu, Bing
    [J]. CHINESE CHEMICAL LETTERS, 2020, 31 (07) : 1863 - 1867
  • [24] Nickel-catalyzed coupling of aryl iodides with aromatic aldehydes: Chemoselective synthesis of ketones
    Huang, YC
    Majumdar, KK
    Cheng, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (05) : 1682 - 1684
  • [25] Cu-based carbene involved in a radical process: a new crossover reaction to construct γ-peroxy esters and 1,4-dicarbonyl compounds
    Jiang, Jiewen
    Liu, Jiajun
    Yang, Ling
    Shao, Ying
    Cheng, Jiang
    Bao, Xiaoguang
    Wan, Xiaobing
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (79) : 14728 - 14731
  • [26] Asymmetric copper-catalyzed C-N cross-couplings induced by visible light
    Kainz, Quirin M.
    Matier, Carson D.
    Bartoszewicz, Agnieszka
    Zultanski, Susan L.
    Peters, Jonas C.
    Fu, Gregory C.
    [J]. SCIENCE, 2016, 351 (6274) : 681 - 684
  • [27] PHOTOCHEMISTRY ON NONREACTIVE AND REACTIVE (SEMICONDUCTOR) SURFACES
    KAMAT, PV
    [J]. CHEMICAL REVIEWS, 1993, 93 (01) : 267 - 300
  • [28] Synthetic Applications of Sulfonium Salts
    Kozhushkov, Sergei I.
    Alcarazo, Manuel
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (26) : 2486 - 2500
  • [29] Recent Advances in Radical Difunctionalization of Simple Alkenes
    Lan, Xing-Wang
    Wang, Nai-Xing
    Xing, Yalan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (39) : 5821 - 5851
  • [30] Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones
    Lan, Xing-Wang
    Wang, Nai-Xing
    Zhang, Wei
    Wen, Jia-Long
    Bai, Cui-Bing
    Xing, Yalan
    Li, Yi-He
    [J]. ORGANIC LETTERS, 2015, 17 (18) : 4460 - 4463