Efficient Syntheses of Diselenides from Selenols

Microwave-assisted one-pot synthesis of symmetrical diselenides, ditellurides and disulfides from organoyl iodides and elemental chalcogen catalyzed by CuO nanoparticles

“…Several methods have been described for the synthesis of diorganoyl diselenides and ditellurides [9][10][11][12][13][14][15][16][17][18] which include the reaction of metal diselenides or ditellurides with organoylhalides [19][20][21], the well established reaction of Grignard reagents with elemental selenium or tellurium, the reduction of selenocyanates [22][23][24][25] and the oxidation of both selenols and selenolates [26,27]. Several methodologies have been described for the synthesis of diorganoyl disulfides generally obtained by oxidation of thiols [28][29][30][31][32][33] or even, according to Taniguchi, from elemental sulfur and aryl iodides catalyzed by Cu-bpy, aluminum and sodium carbonate [34].…”

Improved Method for the Synthesis of Organic Diselenides from Organic Halides under Atmospheric Pressure

“…[11] Organic diselenides also can be prepared by dimerization with selenocyanates [12 -14] or oxidation of selenols. [15] Additionally, Sonoda also reported that elemental selenium can be readily reduced by carbon monoxide (0.5 Mpa) and water in the presence of an organic base to produce hydrogen selenide, which was successfully applied to the synthesis of organic diselenides from alkyl chlorides and acyl chlorides. [16] …”

Highly Efficient Route to Diselenides from the Reactions of Imines and Selenium in the Presence of Carbon Monoxide and Water

“…Both reduction of di-t-butyl selenoketone with NaBH 4 [9] and reaction of benzaldehyde with bis(1,5-cyclooctanediylboryl) [10] produced RSeSeR. Oxidation of selenols with 30% hydrogen peroxide [11] and reduction of aldehydes and ketones with hydrogen selenide [12,13] in the presence of an amine afforded diselenides. Sonoda et al used the Se/CO/H 2 O system for the preparation of diselenides from a very limited number of aliphatic ketones and aldehydes, [14] or acyl chlorides [15] under rather harsh conditions, while aromatic ketones were reduced to hydrocarbons with the same method.…”