Facile Photochemical Transformation of Alkyl Aryl Selenides to the Corresponding Carbonyl Compounds by Molecular Oxygen: Use of Selenides as Masked Carbonyl Groups

Abstract

Alkyl aryl selenides with and without functional groups on the alkyl group were transformed efficiently into the corresponding carbonyl compounds, particularly primary alkyl aryl selenides in good yields, by a simple photolysis in the presence of air or oxygen. This transformation can be conducted without protection of functional groups. The yield of carbonyl compounds was much affected by the solvent viscosity, reaction temperature, concentration of dissolved oxygen in the solvents, wavelength of light, and structure of the aryl substituents. The present study indicates that aryl selenides can be considered as a masked carbonyl group that can be easily converted to a carbonyl group by very mild reaction conditions even in the presence of various unprotected functional groups. Therefore, this functional group transformation can be used as an important tool in organic synthesis due to its simplicity and mild reaction condition.

Engineered Biosynthesis of Alkyne-Tagged Polyketides by Type I PKSs

“…The crude material was purified via flash chromatography (eluting with 9:1 to 7:3 hexanes:ethyl acetate) to provide S2 as a colorless liquid (0.25 g, 43%). The NMR spectra were consistent with previous reports (Hyugano et al, 2008).…”

Bis(trimethylsilyl)selenide in the Selective Synthesis of β‐Hydroxy, β‐Mercapto, and β‐Amino Diorganyl Diselenides and Selenides Through Ring Opening of Strained Heterocycles

“…[11] Diorganyl selenides are also an important class of compounds employed as reagents in organic synthesis. [12] For instance, they are used for the preparation of alkenes, [13] epoxides, [14] aldehydes, and ketones, [15] and as intermediates for the synthesis of organoselenium compounds. [12,16] Different methods for the synthesis of diselenides and selenides have been reported, most of which require multistep procedures.…”

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

“…The authors proposed that the photolysis of 190 , results in a pair of radical species (arylselenyl radical 19 and alkyl radical 192 ). The alkyl radical species 192 undergoes oxidation in the presence of molecular oxygen, forming the corresponding carbonyl compound, while the RSe radical 19 species generates diselenide [76] …”