31536-19-3Relevant academic research and scientific papers
Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
, p. 3863 - 3868 (2016)
A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).
Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones
Pogaku, Naresh,Krishna, Palakodety Radha,Prapurna, Y. Lakshmi
supporting information, p. 1239 - 1249 (2017/07/06)
An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.
Non-expensive, open-flask and selective catalytic systems for the synthesis of sulfinate esters and thiosulfonates
Tranquilino, Arisson,Andrade, Silvia R.C.P.,da Silva, Ana Paula M.,Menezes, Paulo H.,Oliveira, Roberta A.
supporting information, p. 1265 - 1268 (2017/03/10)
Two simple and efficient methods for the synthesis of sulfinate esters and thiosulfonates from sodium salts of sulfinic acids are described. Different alcohols were converted into the corresponding sulfinate esters in good yields and purity in an open flask. By the adjustment of the reaction conditions thiosulfonates could also be obtained in a very short reaction time.
Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access
Huang, Mingming,Hu, Liangzhen,Shen, Hang,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Xiong, Yan
supporting information, p. 1874 - 1879 (2016/04/19)
A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.
Water-soluble polymer-bound, recoverable palladium(0)-phosphine catalysts
Bergbreiter, David E.,Liu, Yun-Shan
, p. 7843 - 7846 (2007/10/03)
The synthesis of a water-soluble polymer-bound Pd(0)-phosphine catalyst is described. This soluble polymeric catalyst is soluble in aqueous or mixed aqueous/organic media and has high activity in nucleophilic allylic substitution and in sp-sp2 coupling reactions of aryl iodides with terminal alkynes. The catalyst can be recycled efficiently by solvent or thermal precipitation methods.
Electrophilic allylation of arenes with in situ generated allyltriarylbismuthonium compound: The Bismuth-mediated polarity inversion of allylsilanes
Matano, Yoshihiro,Yoshimune, Masanori,Suzuki, Hitomi
, p. 7475 - 7478 (2007/10/02)
Reaction of triarylbismuth difluorides 1 with allyltrimethylsilane 2 in CH2Cl2 in the presence of BF3·OEt2 at low temperature generates allyltriarylbismuthonium compound 3 as a pale yellow solution, in which aromatic hydrocarbons and ethers, triphenylphosphine, dimethyl sulfide, p-toluenesulfinate, and thiophenol are all readily allylated to afford the corresponding allyl derivatives in moderate to good yields.
Novel One-Step Preparation of Sulfinic Acid Derivatives from Sulfinic Acid
Furukawa, Mitsuru,Ohkawara, Tadashi,Noguchi, Yoshihide,Nishikawa, Masumi,Tomimatsu, Masahide
, p. 134 - 141 (2007/10/02)
Convenient one-step syntheses of sulfinamides and sulfinate esters from sulfinic acids were achieved by using coupling reagents, such as 2-chloro-1-methylpyridinium iodide, γ-saccharine chloride, N,N'-dicyclohexylcarbodiimide, and diethyl azodicarboxylate and triphenylphosphine.Ammonolysis of sulfinate esters also give sulfinamides.Keyword- sulfinic acid; sulfinamide; sulfinate ester; sulfinyl-transfer reagent; coupling reaction; 2-chloro-1-methylpyridinium iodide; γ-saccharine chloride; N,N'-dicyclohexylcarbodiimide; diethyl azodicarboxylate; triphenylphosphine
