1,2-Alkynyl Functionalization of Unactivated Alkenes via Diverse Radical-Triggered Functional Group Migration

被引:4
|
作者
Sun, Huangbin [1 ]
Jiang, Guofang [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Adv Catalyt Engn Res Ctr,Minist Educ, Changsha 410082, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期
基金
中国国家自然科学基金;
关键词
ACTIVATED ALKENES; DIFUNCTIONALIZATION; ADJACENT; PROTOCOL; RULES;
D O I
10.1021/acs.joc.3c00975
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Wehave developed a transition-metal-free radical approach for1,2-alkynyl functionalization of unactivated alkenes through the combinationof 3-exo-dig cyclization with alkynyl migration triggeredby in situ-generated diverse radical precursors. This strategy providesa robust toolkit to access a variety of synthetically important & alpha;-functionalizedalkynyl ketones, simultaneously installing densely functionalizedcarbonyl, alkynyl, and other various functional groups into the alkenes.The broad substrate scope, which includes distinctly electron-donatingor electron-withdrawing alkynyl migrating groups, excellent functionalgroup compatibility, and remarkable selectivity make this protocolpractical and attractive.
引用
收藏
页码:11661 / 11674
页数:14
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  • [1] Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1,2-Alkynyl Migration
    Zhang, Ping
    Shi, Haonan
    Zhang, Tianshu
    Cai, Peijun
    Jiang, Bo
    Tu, Shujiang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (02) : 423 - 431
  • [2] Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration
    Chen, Dong
    Wu, Zhen
    Yao, Yingming
    Zhu, Chen
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (15): : 2370 - 2374
  • [3] Difunctionalization of Unactivated Alkenes through SCF3 Radical-triggered Distal Functional Group Migration
    Chen Dong
    Ji Meishan
    Yao Yingming
    Zhu Chen
    [J]. ACTA CHIMICA SINICA, 2018, 76 (12) : 951 - 955
  • [4] Photoredox 1,2-dicarbofunctionalization of unactivated alkenes via tandem radical difluoroalkylation and alkynyl migration
    Liu, Jing
    Li, Weipeng
    Xie, Jin
    Zhu, Chengjian
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 797 - 800
  • [5] Hydrogen Radical Initiated 1,2-Alkynyl Migration
    Zhao Qi
    Tu Shu-Jiang
    Jiang Bo
    [J]. ACTA CHIMICA SINICA, 2019, 77 (09) : 927 - 931
  • [6] Oxidative alkylation/alkynylation of terminal alkenes via alkylaldehyde decarbonylation and 1,2-alkynyl migration
    Zhang, Jia-Jia
    Chen, De
    Qin, Yi-Qun
    Deng, Wei
    Luo, Yong-Yue
    Xiang, Jian-Nan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (14) : 3154 - 3158
  • [7] Difunctionalization of alkenes proceeding with radical 1,2-alkynyl migration in batch and continuous-flow modes
    Mao, Ziren
    Zhou, Yiliang
    Zhang, Jingming
    Liu, Chengkou
    Wang, Chang-Sheng
    Yang, Xiaobing
    Qin, Hong
    Fang, Zheng
    Guo, Kai
    [J]. NEW JOURNAL OF CHEMISTRY, 2024, 48 (04) : 1735 - 1740
  • [8] Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
    Qin, Yi-qun
    Chen, De
    Liu, Liang
    Zhang, Jia-jia
    Peng, Xin-ju
    Luo, Yong-yue
    Deng, Wei
    Xiang, Jiannan
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (24): : 4700 - 4708
  • [9] 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
    [J]. ORGANIC LETTERS, 2018, 20 (12) : 3596 - 3600
  • [10] Study on tert-Butyl Radical-Initiated 1,2-Alkynyl Migration
    Zhang, Ping
    Zhang, Tianshu
    Cai, Peijun
    Jiang, Bo
    Tu, Shujiang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (06) : 2408 - 2416