The First Synthesis of Organic Diselenolates: Application to the Synthesis of Diorganyl Diselenides

Abstract

The addition of elemental selenium to organolithium compounds 1 or organic selenates 2 gives organic diselenolates 3. The reactions proceed by the insertion of two selenium atoms into the carbon-metal bonds or of one selenium atom into a selenolate. Evidence for the existence of n-butyldisilenol has also been obtained.

Stable Bromiranium Ions with Weakly‐Coordinating Counterions as Efficient Electrophilic Brominating Agents

“…The solutions were mixed by shaking and submitted to NMR measurements. Corresponding experiments were also carried out with tetrahydrothiophene, thioanisole and dibutylselenide [28] in place of diethylsulfide (see supporting information for details and NMR spectra). Thiiranium ion 7: 2-BArF (125 mg, 0.1 mmol) was placed in a2mL glass vial and dissolved in CH 2 Cl 2 (1 mL).…”

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

“…[17] Unsymmetrical organoselenides can be accessed from selenazole derivatives [18] or benzeneselenol in the presence of cesium bases and alkyl halides. [19] Oxidation of selenols, [20] alkylation of selenolates [21] to diselenides or selenides, and dimerization with selenocyanates are commonly used procedures. Cross-coupling of selenium and aryl halides catalyzed by CuO nanoparticles leads to a variety of symmetrical diselenides through a one-pot coupling-reduction procedure.…”

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

“…After the optimization of the best solvent and base, other important parameters were studied, such as the reaction time, microwave irradiation (power) and temperature (Table 2, entries [10][11][12][13][14][15][16]. When the reaction time was reduced from 10 to 7 min of irradiation no significant decline in the yield was observed (entries 1 and 10).…”

“…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].…”