Metal-Free Three-Component Oxyalkynylation of Alkenes

被引：26
|
作者：
Li, Yangshan [1 ]
Lu, Ran [1 ]
Sun, Shutao [1 ]
Liu, Lei [1 ,2 ]
机构：
[1] Shandong Univ, Sch Pharmaceut Sci, Jinan 250012, Shandong, Peoples R China
[2] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 21期
基金：
美国国家科学基金会;
关键词：
NUCLEOPHILE-OLEFIN COMBINATION; AROMATIC-SUBSTITUTION REACTION; ANTI-MARKOVNIKOV ADDITION; PHOTOCHEMICAL NUCLEOPHILE; ACIDS; DIFUNCTIONALIZATION; EFFICIENT; RADICALS; ALCOHOLS; STYRENES;
D O I：
10.1021/acs.orglett.8b02954
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented (NH4)(2)S2O8 mediated metal-free three-component alkene oxyalkynylation using H2O or alcohol as oxygenation agent is described. Mechanistic studies suggested that the reversed regioselectivity should be dictated by an alkene radical cation intermediate.
引用
收藏
页码：6836 / 6839
页数：4
相关论文
共 50 条
  • [1] Metal-free three-component amino- and carbotrideuteromethylthiolation of alkenes in water
    Han, Siyu
    Zhao, Lin
    Zhou, Xinyu
    Zhang, Kemeng
    Ma, Yunfei
    Wu, Ge
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (21): : 6064 - 6068
  • [2] Metal-Free Three-Component Oxyazidation of Alkenes with Trimethylsilyl Azide and N-Hydroxyphthalimide
    Xia, Xiao-Feng
    Gu, Zhen
    Liu, Wentao
    Wang, Haijun
    Xia, Yongmei
    Gao, Haiyan
    Liu, Xiang
    Liang, Yong-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 290 - 295
  • [3] Three-Component Metal-Free Arylation of Isocyanides
    Basavanag, Unnamatla M. V.
    Dos Santos, Aurelie
    El Kaim, Laurent
    Gamez-Montano, Rocio
    Grimaud, Laurence
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7194 - 7197
  • [4] Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System
    Huang, Jiawei
    Li, Xiaoman
    Xu, Liang
    Wei, Yu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3054 - 3067
  • [5] Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates
    Zhang, Jitan
    Liang, Zhenda
    Wang, Jun
    Guo, Ziyi
    Liu, Changqing
    Xie, Meihua
    ACS OMEGA, 2018, 3 (12): : 18002 - 18015
  • [6] Visible-Light-Induced Metal-Free Three-Component Amidoheteroarylation of Alkenes to Synthesize β-(Hetero)arylethylamines
    Feng, Qiange
    Wang, He
    Liu, Yang
    Wei, Lin
    Sun, Jing
    Wang, Xin
    Sun, Ran
    Wang, Yujia
    Li, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (19)
  • [7] Metal-Free Three-Component Regioselective Aminofluorination of Styrene Derivatives
    Zhang, Qiao
    Zheng, Guangfan
    Zhang, Qian
    Li, Yan
    Zheng, Qan
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15): : 8258 - 8266
  • [8] Metal-Free Decarboxylative Three-Component Coupling Reaction for the Synthesis of Propargylamines
    Park, Kyungho
    Heo, Yumi
    Lee, Sunwoo
    ORGANIC LETTERS, 2013, 15 (13) : 3322 - 3325
  • [9] Chemoselective three-component synthesis of α-carbolines under metal-free conditions
    Feng, Wei
    Zhang, Chao
    Zhou, Xinlin
    You, Kuiyi
    Deng, Guo-Jun
    Chen, Shanping
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) : 5457 - 5462
  • [10] A three-component approach to isoxazolines and isoxazoles under metal-free conditions
    Wang, Dahan
    Zhang, Feng
    Xiao, Fuhong
    Deng, Guo-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (41) : 9163 - 9168
12345