Organoselenium-Catalyzed Oxidative C═C Bond Cleavage: A Relatively Green Oxidation of Alkenes into Carbonyl Compounds with Hydrogen Peroxide

Abstract

A relatively green oxidative C═C bond cleavage of alkenes was achieved by organoselenium-catalyzed alkene oxidation reaction in ethanol with hydrogen peroxide, affording carbonyl compounds under relatively mild conditions. It is a new reaction style for the organoselenium-catalyzed oxidation of alkenes and largely contributes to the growing field of organoselenium catalysis.

Design and Preparation of Poly‐Selenides: Easily Fabricated and Efficient Organoselenium Materials for Heavy Metal Removing and Recycling

“…The material was initially tested in the oxidative alkene scission reaction and ketoxime deoximation as a heterogeneous catalyst. However, it was found to be less reactive than homogeneous organoselenium catalysts, [7a,b] affording the ketone products in very low yield, while most of the substrates were not converted (Scheme , equations (3‐4)).…”

“…Yet, selenium chemistry has attracted chemists for a long time, mainly because of the particular bioactivities of the organoselenium compounds as well as their versatile reactivities in organic synthesis . Recently, the green‐side of selenium began to be realized and organoselenium‐catalyzed reactions drew much attention for their application potential in industrial productions . During the last three years, we have reported a variety of organoselenium‐catalyzed green transformations .…”

“…Recently, the green‐side of selenium began to be realized and organoselenium‐catalyzed reactions drew much attention for their application potential in industrial productions . During the last three years, we have reported a variety of organoselenium‐catalyzed green transformations . Compared with transition metals, the selenium element is eco‐safe because it is an important and necessary trace element for human beings and can be metabolized in the body [5a,9,10] .…”

Selenium reagents as catalysts

“…35 Recently, Yu and co-workers demonstrated a highly efficient selenium-catalysed approach for the oxidative cleavage of terminal alkenes 27 using 5.0 mol% of dialkyl diselenide 28 in the presence of hydrogen peroxide using environmentally friendly solvent ethanol. 40 The cleavage reactions were found quite slow but carbonyl products 5 were isolated in useful yields (Scheme 8). Various dialkyl diselenides 28 were investigated during these oxidations and dicyclohexyl diselenide 28 (R = c-C6H11) exhibited best catalytic activity.…”

A cost‐effective shortcut to prepare organoselenium catalysts via decarboxylative coupling of phenylacetic acid with elemental selenium

“…Recently, much attention has been paid to the eco‐friendly aspects of organoselenium chemistry and among reported works, organoselenium catalysis is one of the most important research directions for its clean procedures, transition‐metal‐free reaction conditions and the metabolizable catalytic Se element that affords a potential alternative to transition metal catalysts . Researchers have reported a series of organoselenium‐catalyzed reactions and this field has seen rapid progress in recent years . However, up to the present, the frequently used method for introducing Se into molecules to synthesize Se catalysts is via the Grignard reagent reaction, which is very tedious to operate and suffers from the use of carcinogenic organohalide starting materials that are hazardous to the environment (Scheme ).…”