Electrochemically Mediated Fixation of CO₂: Synthesis of Functionalized Oxazolidine‐2,4‐Diones by Three‐Component Reactions

Abstract

Carbon dioxide is a harmful greenhouse gas, as well as a valuable resource. Here, a three‐component cyclization reaction was developed for the synthesis of oxazolidine‐2,4‐diones by immobilizing CO2 under the electrochemistry and copper catalyst. Propargyl amide was used as the reaction substrate to capture carbon dioxide to produce carboxyl anion, while selenide produced electrophilic receptor to activate the triple bond under electrochemical conditions. Then, intramolecular cyclization reaction was carried out to obtain the target product. Through this environmentally friendly strategy, a series of important oxazolidine‐2,4‐diones was synthesized.

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

“…87 Liang, Pan and coworkers recently reported a three-component cyclization reaction for the synthesis of functionalized oxazolidine-2,4-diones (Scheme 36). 88 In this reaction, propargyl amide was used as the reaction substrate to capture carbon dioxide to produce carboxyl anion in the presence of K 2 CO 3 , while diselenide produced electrophilic receptor to activate the triple bond under electrochemical conditions. Then, intramolecular cyclization reaction was carried out to give the target selenated oxazolidine-2,4-dione.…”

Organo-catalyzed C2,3–H aminochalcogenation of indoles with secondary (aliphatic) amines

“…In sharp contrast, the three-component coupling reaction presents more significant challenges compared to the first two strategies, mainly due to its complicated nature involving multiple steps and reactants. 6 Thus, if the challenges associated with the three-component coupling reaction, including selectivity, compatibility, scalability and retrosynthetic analysis, can be successfully addressed, it would undoubtedly herald a significant leap forward in the field of organic synthesis.…”

Transition-metal-free four-component reaction of nitriles and disulfides/diselenides

“…14 On the other hand, organochalcogens display various chemical and biological properties, 15 thus the installation of a chalcogen-containing moiety into the 4-aminopyrimidine scaffolding would be very meaningful for new drug discovery. 16 In connection with our efforts on organochalcogen chemistry, 17 we disclose a four-component reaction of nitriles and disulfides/diselenides in the presence of t -BuOK and K 2 S 2 O 8 , offering a straightforward synthetic route to sulfurized/selenated 4-aminopyrimidines.…”