Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides

Abstract

The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.

Preparation of Oxazole Acetals from N‐Propargylamides Enabled by Visible‐Light‐Promoted Selenium‐π‐Acid Catalysis

“…Using catalytic oxidant and air mixture system provides new ideas for the development of efficient green oxidation methods in the future. Based on our group in the field of visible light aerobic oxidation induced a series of achievements, [14] as a continuation of our studies on organoselenium compounds [15] . We developed synthesis of oxazole acetals in one pot using catalytic N−F/diselenides system under photocatalytic aerobic conditions (Scheme 1b).…”

Electrifying green synthesis: recent advances in electrochemical annulation reactions

“…According to cyclic voltammetry analysis, oxidation and reduction peaks of diphenyl diselenide were observed at 1.8 V and −1.5 V vs. Ag/AgCl, respectively. Thus, considering the control reactions and the results reported in the literature, 114,115 the authors suggest a mechanism route via a radical intermediate. Diphenyl diselenide is reduced at the cathode to give an anion radical as an intermediate, which is further decomposed to give the phenyl-selenium radical and phenyl-selenium anion.…”

Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes

“…Later, the group of Liu developed a visible light-driven selenocyclization of N-allylamides in MeCN in the presence of 2 mol% 4CzIPN under visible-light and in air (Scheme 20). 29 While dihydroisoxazole was produced in 73% yield without any photocatalyst under these optimized reaction conditions, the use of 4CzIPN as a photocatalyst promoted the reaction process. In contrast to other seleno cylization reactions, this protocol only needed 60 mol% diselenides.…”