Electrochemical Difunctionalization of Alkenes: Simultaneous Construction of C–Se and C–S Bonds

Abstract

Electrochemical oxidation of alkene difunctionalization with simultaneous construction of C−Se and C−S bonds is reported. The products of β-selenylethyl dithiocarbamates are obtained with CS 2 , amines, alkenes, and diphenyl diselenides in the absence of any oxidant or metal. Furthermore, the transformation is compatible with various groups. In the preliminary mechanism studies, we propose three possible pathways.

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

“…Recently, Dong et al accomplished an electrochemical oxidation strategy to prepare β-selenylethyl dithiocarbamates from CS 2 , 107 amines, alkenes, and diphenyl diselenides without oxidant or metal (Scheme 97). 108 Aliphatic alkenes, such as cyclohexene, cyclopentene, and allylbenzene, were well tolerated in in this transformation, giving the desired products in good yields. Cyclic secondary amines including pyrrolidine and piperidine are proved to be suitable substrates.…”

Advances in Difunctionalization of Olefins with Diorganyl Dichalcogenides

“…In 2023, Dong's group reported a region-selective electrochemical four-component difunctional selenylation of olefins for synthesis of a series of β-selenethyldithiocarbamate products (Scheme 30). [44] It is reported that this method was compatible with both electron-withdrawing and electrondonating groups. But this reaction of CS 2 , amines, olefins, and diaryl diselenides only afforded the products with mild yields of 35-63 %.…”

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

“…37 An electrochemical method for the synthesis of β-selenylethyl dithiocarbamates was recently developed by Dong and Ren et al (Scheme 10). 38 This protocol employed n Bu 4 NBF 4 as the supporting electrolyte and K 2 CO 3 as a base in CH 3 CN at ambient temperature. Several control experiments were performed to gain mechanistic insights.…”