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  

作　　者：Mingxuan Liu Yiming Li Lei Yu Qing Xu Xuefeng Jiang 

机构地区：[1]Institute of Pesticide, School of Chemistry and Chemical Engineering and School of Horticulture and Plant Protection, Yangzhou University [2]Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University

出　　处：《Science China Chemistry》2018年第3期294-299,共6页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(21202141,21672069);Priority Academic Program Development of Jiangsu Higher Education Institutions;the Open Project Program of Jiangsu Key Laboratory of Zoonosis(R1509);the High Level Talent Support Project of Yangzhou University

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 α-alkoxyl selenides in the presence of only 0.5 equiv. of H_2O_2. Controlling the sub-stoichiometric H_2O_2 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.Under iodine-catalyzed and visible light-irradiated aerobic conditions, selenoalkoxylation of olefins with diselenides and alcohols can be efficiently achieved to afford the useful α-alkoxyl selenides in the presence of only 0.5 equiv. of H_2O_2. Controlling the sub-stoichiometric H_2O_2 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.

关 键 词：selenium alkoxyl selenide aerobic oxidation visible light iodine catalysis 

分 类 号：O627.61[理学—有机化学]