Difunctionalization of alkenes proceeding with radical 1,2-alkynyl migration in batch and continuous-flow modes

被引:1
|
作者
Mao, Ziren [1 ]
Zhou, Yiliang [1 ]
Zhang, Jingming [1 ]
Liu, Chengkou [1 ]
Wang, Chang-Sheng [1 ]
Yang, Xiaobing [2 ]
Qin, Hong [1 ]
Fang, Zheng [1 ]
Guo, Kai [1 ,3 ]
机构
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China
[2] Jiangsu Ind Technol Res Inst, China Biol & Med Dept, Nanjing 210031, Peoples R China
[3] Nanjing Tech Univ, State Key Lab Mat Oriented Chem Engn, Nanjing 211816, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
UNACTIVATED ALKENES; METAL-FREE;
D O I
10.1039/d3nj05081e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient strategy to construct alpha-alkynyl ketones through electrochemical difunctionalization of alkenes was developed. This method is oxidant-free, metal-free, high-efficiency and eco-friendly, and offers rapid constructions of 1,2-alkynyl migration products through the radical process of 3-exo-dig cyclization. Moreover, the reaction could undergo a successful transformation under continuous-flow conditions. A straightforward method for electrochemical difunctionalization of alkenes to construct the corresponding alpha-alkynyl ketone product under catalyst- and oxidant-free conditions in batch and continuous-flow modes was developed.
引用
收藏
页码:1735 / 1740
页数:6
相关论文
共 50 条
  • [21] Synthesis of Highly Substituted 3-Formylfurans by a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization Cascade
    Wang, Tao
    Shi, Shuai
    Hansmann, Max M.
    Rettenmeier, Eva
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (14) : 3715 - 3719
  • [22] Lipase-catalyzed kinetic resolution of 2-methylene-substituted cycloalkanols in batch and continuous-flow modes
    Tomin, Anna
    Hornyanszky, Gabor
    Kupai, Katalin
    Dorko, Zsanett
    Urge, Laszlo
    Darvas, Ferenc
    Poppe, Laszlo
    PROCESS BIOCHEMISTRY, 2010, 45 (06) : 859 - 865
  • [23] STUDIES ON ISOLATED RAT ADRENAL-CELLS .1. CONTINUOUS-FLOW AND BATCH INCUBATIONS
    FALKE, HE
    DEGENHART, HJ
    ABELN, GJA
    VISSER, HKA
    CROUGHS, RJM
    ACTA ENDOCRINOLOGICA, 1975, 78 (01): : 110 - 121
  • [24] Radical-Mediated 1,2-Difunctionalization of Alkenes with Nucleophiles and Acetonitrile through C(sp3)-H Bond Cleavage
    Zhu, Fengxiang
    Yang, Yifan
    Shi, Shanshan
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (01) : 56 - 61
  • [25] Electrosynthesis of Highly Functionalized Polycyclic N-Heteroaromatics through Cascade Radical Cyclization and Alkoxylation in Batch and Continuous-Flow
    Chen, Jiawei
    Qiao, Yaqi
    Guan, Wenjing
    Yuan, Chengcheng
    Yao, Yifei
    Fang, Zheng
    Zhao, Yue
    Liu, Chengkou
    Guo, Kai
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2023, 11 (50) : 17728 - 17738
  • [26] Immobilized lipase screening towards continuous-flow kinetic resolution of (±)-1,2-propanediol
    Aguillon, Anderson R.
    Avelar, Marcelo N.
    Gotardo, Larissa E.
    de Souza, Stefania P.
    Leao, Raquel A. C.
    Itabaiana Jr, Ivaldo
    Miranda, Leandro S. M.
    de Souza, Rodrigo O. M. A.
    MOLECULAR CATALYSIS, 2019, 467 : 128 - 134
  • [27] UV Light-Mediated Difunctionalization of Alkenes through Aroyl Radical Addition/1,4-/1,2-Aryl Shift Cascade Reactions
    Zheng, Lewei
    Huang, Hongli
    Yang, Chao
    Xia, Wujiong
    ORGANIC LETTERS, 2015, 17 (04) : 1034 - 1037
  • [28] Synthesis of Highly Substituted N-(Furan-3-ylmethylene)benzenesulfonamides by a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization Cascade
    Wang, Tao
    Huang, Long
    Shi, Shuai
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (45) : 14868 - 14871
  • [29] Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade
    Wang, Tao
    Shi, Shuai
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (10) : 2337 - 2342
  • [30] Immobilization of Phenylalanine Ammonia-Lyase on Single-Walled Carbon Nanotubes for Stereoselective Biotransformations in Batch and Continuous-Flow Modes
    Bartha-Vari, Judith H.
    Tosa, Monica I.
    Irimie, Florin-Dan
    Weiser, Diana
    Boros, Zoltan
    Vertessy, Beata G.
    Paizs, Csaba
    Poppe, Laszlo
    CHEMCATCHEM, 2015, 7 (07) : 1122 - 1128