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

Mingxuan Liu^1,2, Yiming Li²,Lei Yu^1,*,Qing Xu¹& Xuefeng Jiang^2,*

1Institute of Pesticide, School of Chemistry and Chemical Engineering and School of Horticulture and Plant Protection, Yangzhou University

2Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University

Abstract: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 H₂O₂. Controlling the sub-stoichiometric H₂O₂amount is crucial to avoid the non-selectiveover-oxidation of the diselenides that leads to theineffective hyper-valent selenium compounds. Meanwhile, under visible light irradiation, the green, safe, and low-cost air canwork 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 theproducts.

Science China Chemistry,2017,60,1–2. IF=4.132

文章链接:http://engine.scichina.com/publisher/scp/journal/SCC/doi/10.1007/s11426-017-9158-y?slug=abstract