831-91-4Relevant articles and documents
Takahashi,Y. et al.
, p. 415 - 421 (1972)
A CONVENIENT PREPARATION OF ARYLTHIOSTANNANES
Li, C.-J.,Harpp, David N.
, p. 7293 - 7294 (1992)
Arylthiostannanes 1 can be prepared in excellent yield by the reaction of diaryldisulfides 2 with bis(triphenylstannyl)telluride (3c) under mild conditions.In addition, the use of telluride 3c with aryl disulfides in the presence of fluoride ion and benzyl bromide gives a one-pot synthesis of unsymmetrical sulfides.
Gold-catalyzed thioetherification of allyl, benzyl, and propargyl phosphates
Miura, Hiroki,Nishio, Hidenori,Shishido, Tetsuya,Toyomasu, Tomoya
, p. 1109 - 1116 (2022/03/02)
Gold-catalyzed thioetherification of C(sp3)-O bonds is described. The reaction of allyl phosphates and thiosilanes in the presence of gold nanoparticles supported on ZrO2 proceeded efficiently under mild reaction conditions to give the corresponding allyl sulfides in excellent yields. ZrO2-Supported gold nanoparticles showed excellent catalytic turnover and reusability. In addition, the C-O bonds of benzyl and propargyl phosphates underwent thioetherification to afford benzyl and propargyl sulfides. The reaction of an optically active benzyl phosphate proceeded with excellent chirality transfer to give a benzyl sulfide with high enantiomeric purity. Control experiments corroborated that soluble gold species were responsible for the efficient thioetherification of C-O bonds of phosphates, and characterization of the catalysts revealed that cationic gold species at the surface of gold nanoparticles supported on ZrO2 served as a source for highly active catalytic species.
Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis
Camaj, David,Carlsson, Robin,Dalla-Santa, Oscar,Lill, Malin,Lundberg, Helena,Margarita, Cristiana,Ramstr?m, Anja,Tu?on, Hernando,Villo, Piret
, p. 7420 - 7430 (2021/11/23)
Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
