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
  • [1] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis
    Aggarwal, VK
    Winn, CL
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 611 - 620
  • [2] Visible light promoted cross-dehydrogenative coupling: a decade update
    Bagdi, Avik Kumar
    Rahman, Matiur
    Bhattacherjee, Dhananjay
    Zyryanov, Grigory V.
    Ghosh, Sumit
    Chupakhin, Oleg N.
    Hajra, Alakananda
    [J]. GREEN CHEMISTRY, 2020, 22 (20) : 6632 - 6681
  • [3] Osmium-free direct syn-dihydroxylation of alkenes
    Bataille, Carole J. R.
    Donohoe, Timothy J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) : 114 - 128
  • [4] Site-selective and versatile aromatic C-H functionalization by thianthrenation
    Berger, Florian
    Plutschack, Matthew B.
    Riegger, Julian
    Yu, Wanwan
    Speicher, Samira
    Ho, Matthew
    Frank, Nils
    Ritter, Tobias
    [J]. NATURE, 2019, 567 (7747) : 223 - 228
  • [5] Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis
    Chen, Cheng
    Wang, Minyan
    Lu, Hongjian
    Zhao, Binlin
    Shi, Zhuangzhi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (40) : 21756 - 21760
  • [6] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1911 - 1923
  • [7] Practical and sustainable approach for clean preparation of 5-organylselanyl uracils
    Chen, Jin-Yang
    Zhong, Chun-Tao
    Gui, Qing-Wen
    Zhou, Yuan-Ming
    Fang, Yang-Yang
    Liu, Kai-Jian
    Lin, Ying-Wu
    Cao, Zhong
    He, Wei-Min
    [J]. CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 475 - 479
  • [8] Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling
    Chen, Jun
    Liang, Yu-Jie
    Wang, Peng-Zi
    Li, Guo-Qing
    Zhang, Bin
    Qian, Hao
    Huan, Xiao-Die
    Guan, Wei
    Xiao, Wen-Jing
    Chen, Jia-Rong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (33) : 13382 - 13392
  • [9] Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
    Chen, Junting
    Li, Jiakun
    Plutschack, Matthew B.
    Berger, Florian
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5616 - 5620
  • [10] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids
    Chu, Lingling
    Lipshultz, Jeffrey M.
    MacMillan, David W. C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7929 - 7933