Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides

被引:65
|
作者
Liu, Mingxuan [1 ,2 ,3 ]
Li, Yiming [3 ]
Yu, Lei [1 ,2 ]
Xu, Qing [1 ,2 ]
Jiang, Xuefeng [3 ]
机构
[1] Yangzhou Univ, Inst Pesticide, Sch Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
[2] Yangzhou Univ, Sch Hort & Plant Protect, Yangzhou 225002, Jiangsu, Peoples R China
[3] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
selenium; alkoxyl selenide; aerobic oxidation; visible light; iodine catalysis; BAEYER-VILLIGER OXIDATION; PHOTOREDOX CATALYSIS; DIPHENYL DISELENIDE; DIARYL DISELENIDES; CARBOXYLIC-ACIDS; ALKENES; PHOTOCATALYSIS; METHYLENECYCLOPROPANES; CYCLIZATION; AMINATION;
D O I
10.1007/s11426-017-9158-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Under iodine-catalyzed and visible light-irradiated aerobic conditions, selenoalkoxylation of olefins with diselenides and alcohols can be efficiently achieved to afford the useful alpha-alkoxyl selenides in the presence of only 0.5 equiv. of H2O2. Controlling the sub-stoichiometric H2O2 amount is crucial to avoid the non-selective over-oxidation of the diselenides that leads to the ineffective hyper-valent selenium compounds. Meanwhile, under visible light irradiation, the green, safe, and low-cost air can work as a supplemental mild oxidant in the reaction to ensure selective oxidation of the diselenides, full conversion of the reactants, and ultimately good yield of the products.
引用
收藏
页码:294 / 299
页数:6
相关论文
共 3 条
  • [1] Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides
    Mingxuan Liu
    Yiming Li
    Lei Yu
    Qing Xu
    Xuefeng Jiang
    Science China(Chemistry) , 2018, (03) : 294 - 299
  • [2] Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides
    Mingxuan Liu
    Yiming Li
    Lei Yu
    Qing Xu
    Xuefeng Jiang
    Science China(Chemistry), 2018, 61 (03) : 294 - 299
  • [3] Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides
    Mingxuan Liu
    Yiming Li
    Lei Yu
    Qing Xu
    Xuefeng Jiang
    Science China Chemistry, 2018, 61 : 294 - 299