Synthesis of Organoselenium Compounds with Elemental Selenium

Recent advances in organic synthesis applying elemental selenium

The one-pot multicomponent synthetic strategy of organoselenium compounds represents an alternative and robust protocol to the conventional multistep methods. During the last decade, a potential advance has been made in this domain. This review discusses the latest advances in the polymerization, metal, and metal-free one-pot multicomponent synthesis of organoselenium compounds.

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One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

Tetramethylammonium trifluoromethylselenate ([Me4N][SeCF3]) has been confirmed as an excellent precursor of selenofluorophosgene for amines in the preparation of selenocarbamoyl fluorides, selenoureas, and heterocycles under catalyst- and additive-free conditions. Reactions of [Me4N][SeCF3] with secondary amines at room temperature provided exclusively selenocarbamoyl fluorides in moderate to high yields, while the same reactions with primary amines afforded selenoureas in good yields. When [Me4N][SeCF3] was similarly mixed with amines containing adjacent amino, hydroxyl or thiol groups, five- and six-membered heterocycles were produced. The reaction featured simplicity, rapidness, high efficiency, a broad substrate scope, and good functional group tolerance, offering a convenient access to a variety of selenocarbonylated compounds, which were otherwise difficult to synthesize by other approaches.

Facile synthesis of selenocarbamyl fluorides, selenoureas and their derivatives with [Me4N][SeCF3]

A one-pot four-component synthesis of diselenocarbamates was established from the combination of diselanes, selenium powder, chloroform and amines under mild conditions. A total of 36 diselenocarbamates were achieved in a straightforward manner in up to 91% yield. The zwitterionic intermediate [R2R3NCHCl]+Cl−, formed from chloroform and amine in the presence of a base, was captured by diselane via nucleophilic substitution to afford the intermediate [R2R3NCHSeR1]+Cl−. With the help of a base, the desired diselenocarbamate was successfully achieved through a carbene intermediate [(R2R3N)(SeR1)C:] with selenium powder.

One-pot four-component assembly for diselenocarbamates

An efficient and practical method for the straightforward construction of unsymmetrical selenoureas and cycloselenoureas via the combination of selenium powder, chloroform, and two different amines...

Lai Li

Papers

One-Pot Four-Component Assembling for Selenoureas.

One-pot four-component assembly for diselenocarbamates