14790-33-1Relevant academic research and scientific papers
Metal-Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated in Situ Generation of Sulfinate Anion
Omer, Humair M.,Liu, Peng,Brummond, Kay M.
, p. 7959 - 7975 (2020/07/15)
Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to fo
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.
Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
supporting information, p. 3863 - 3868 (2016/12/16)
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.).
Silver-catalyzed rearrangement of propargylic sulfinates to allenic sulfones
Harmataa, Michael,Huanga, Chaofeng
experimental part, p. 972 - 974 (2009/05/27)
Treatment of propargylic sulfinate esters with 2 mol% of silver hexafluoroantimonate results in the rapid formation of allenic sulfones in essentially quantitative yield.
Synthesis of thiophenes from allenyl sulfones involving α,β-unsaturated sulfines as intermediates
Linden, Johannes B. van der,Asten, Peter F. T. M. van,Braverman, Samuel,Zwanenburg, Binne
, p. 51 - 60 (2007/10/02)
The synthesis of thiophenes starting from allenyl sulfones, via intermediate formation of α,β-unsaturated sulfines, is described.The allenyl sulfones were synthesized by a -sigmatropic rearrangement of appropriately substituted prop-2-ynyl sulfinates
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
