The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides

A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids

“…As shown in Scheme , the alkylation of 6 was performed under phase-transfer catalysis in THF using aqueous sodium hydroxide (6%), CTACl as a catalyst, and the alkyl bromide (benzyl bromide and allyl bromide). The use of aminoiminomethanesulfinic acid in the reaction mixture led to the reduction of disulfides 6 to the corresponding thiol, which was not isolated, and instead was directly alkylated. The hydrolytic conditions produced the acids 7 in satisfactory yields.…”

Synthesis of Thiol Esters Using Nano CuO/Ionic Liquid as an Eco‐Friendly Reductive System Under Microwave Irradiation

“…This avoids the use of reagents with unpleasant odors such as thiols 9. Most of the methods described for the reduction of S–S bonds use reagents such as hydroxide,10 hydrazine,11 sodium hydrogen telluride,12 [BnEt 3 N] 2 MoS 4 ,13 or expensive metals including indium salts 14. The development of new synthetic strategies to improve these transformations is currently an area of great interest.…”

Zinc-Mediated Synthesis of Diaryl Selenides from Diaryl Diselenides and Diaryliodonium Salts in Aqueous Media

“…Diaryl selenides, containing amino groups, have useful antioxidative properties [2], and some biologically active molecules include diarylselenium moiety [3]. Among the useful and general methods for the preparation of symmetrical and unsymmetrical diaryl selenides, we can cite those involving the treatment of arenediazonium salts with sodium selenide [4] and with sodium benzeneselenolate [5], the reaction of electrophilic selenium species such as diselenides and selenocyanates with Grignard reagents and aryllithiums [6], the arylation of sodium benzeneselenolate with an aryl halide catalyzed by nickel (II) complex [7], photochemical reaction of simple haloarenes with sodium areneselenolate [8], the reaction of diaryl diselenides with activated halides in the presence of aminoiminomethanesulfinic acid [9], copper-catalyzed reaction of aryl iodide and diphenyl diselenide using magnesium metal [10], palladium-catalyzed reactions of phenyltributylstannyl selenide (PhSeSnBu 3 ) with aryl halides and triflates [11]. However, some of these methods suffer from disadvantages such as the use of toxic, hazardous, expensive or less easily available reagents, harsh reaction conditions or lower yields.…”