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
来源：
NEW JOURNAL OF CHEMISTRY | 2024年 / 48卷 / 04期
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
  • [11] Switchable electrosynthesis of furoquinones in batch and continuous-flow modes
    Yuan, Chengcheng
    Huang, Xiangxing
    Qiao, Yaqi
    Guan, Wenjing
    Liu, Chengkou
    Fang, Zheng
    Li, Yuguang
    Guo, Kai
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (09) : 2310 - 2317
  • [12] Alkene 1,2-Difunctionalization by Radical Alkenyl Migration
    Tang, Xinjun
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (03) : 814 - 817
  • [13] Photoredox 1,2-dicarbofunctionalization of unactivated alkenes via tandem radical difluoroalkylation and alkynyl migration
    Liu, Jing
    Li, Weipeng
    Xie, Jin
    Zhu, Chengjian
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 797 - 800
  • [14] Iron-Promoted Difunctionalization of Alkenes by Phenylselenylation/1,2-Aryl Migration
    Wu, Ping
    Wu, Kaikai
    Wang, Liandi
    Yu, Zhengkun
    ORGANIC LETTERS, 2017, 19 (19) : 5450 - 5453
  • [15] Merging "Anti-Baldwin" 3-Exo-Dig Cyclization with 1,2-Alkynyl Migration for Radical Alkylalkynylation of Unactivated Olefins
    Zhao, Qi
    Ji, Xiao-Shuang
    Gao, Yi-Yun
    Hao, Wen-Juan
    Zhang, Ke-Ying
    Tu, Shu-Jiang
    Jiang, Bo
    ORGANIC LETTERS, 2018, 20 (12) : 3596 - 3600
  • [16] 1,2-Difunctionalization-type (hetero) arylation of unactivated alkenes triggered by radical addition/remote (hetero) aryl migration
    Li, Lei
    Gu, Qiang-Shuai
    Wang, Na
    Song, Ping
    Li, Zhong-Liang
    Li, Xiao-Hua
    Wang, Fu-Li
    Liu, Xin-Yuan
    CHEMICAL COMMUNICATIONS, 2017, 53 (28) : 4038 - 4041
  • [17] Batch and Continuous-Flow Electrochemical Geminal Difluorination of Indeno[1,2-c]furans
    Yuan, Guo-Cai
    Gao, Fang-Ling
    Liu, Kang-Wei
    Li, Minggang
    Lin, Yuqi
    Ye, Ke-Yin
    ORGANIC LETTERS, 2024, 26 (28) : 6059 - 6064
  • [18] Silver-catalyzed oxidative alkylation/alkynylation of 1,4-enynyl-3-ols with alkylbromides through radical 1,2-alkynyl migration
    Chen, De
    Zhang, Nianqi
    Liang, Qiuju
    Deng, Wei
    Xiao, Zhiyi
    Dong, Wanrong
    Xiang, Jiannan
    CATALYSIS COMMUNICATIONS, 2024, 186
  • [19] Metal-Free Direct 1,6-and 1,2-Difunctionalization Triggered by Radical Trifluoromethylation of Alkenes
    Huang, Lin
    Zheng, Sheng-Cai
    Tan, Bin
    Liu, Xin-Yuan
    ORGANIC LETTERS, 2015, 17 (06) : 1589 - 1592
  • [20] Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes
    Li, Zhong-Liang
    Fang, Gui-Chun
    Gu, Qiang-Shuai
    Liu, Xin-Yuan
    CHEMICAL SOCIETY REVIEWS, 2020, 49 (01) : 32 - 48
12345