28195-10-0Relevant academic research and scientific papers
Sulfur Assisted Tandem Electrophilic Fluorinative Deacylation: Synthesis of α-Fluoro β-Ketosulfides
Varun, Begur Vasanthkumar,Prabhu, Kandikere Ramaiah
, p. 9525 - 9536 (2017/09/23)
A successful synthesis of α-fluoro-β-ketosulfides using an electrophilic fluorination method has been reported for the first time. The reaction proceeds via an electrophilic fluorination of α-sulfenyl-β-diketones followed by an unexpected tandem deacylation. The resulting products, α-fluoro-β-ketosulfides, are easily oxidized to the corresponding α-fluoro-β-ketosulfones, which can be used for further useful olefination reactions.
Iodine-catalyzed C-H/S-H oxidative coupling: From 1,3-diketones and thiophenols to β-dicarbonyl thioethers
Cao, Hao,Yuan, Jiwen,Liu, Chao,Hu, Xinquan,Lei, Aiwen
, p. 41493 - 41496 (2015/05/27)
A novel method on iodine-catalyzed oxidative coupling between 1,3-diketones and thiophenols to form β-dicarbonyl thioethers was developed. The C-S bond was supposed to be formed via a radical substitution pathway instead of the usual nucleophilic substitu
Sulfenylation of β-Diketones Using C- H Functionalization Strategy
Varun, Begur Vasanthkumar,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 2944 - 2947 (2015/06/30)
Sulfenylation of β-diketones is challenging as β-diketones undergo deacylation after sulfenylation in the reaction medium. The sulfenylation of β-diketones without deacylation under metal-free conditions at ambient temperature via a cross dehydrogenative coupling (CDC) strategy is reported. The resultant products can be further manipulated to form α,α-disubstituted β-diketones and pyrazoles.
Facile carbon-sulfur bond cleavage in diarylsulfonium ylides: A catalytic sulfur-to-silicon group transfer
Huang, Xueliang,Goddard, Richard,Maulide, Nuno
supporting information, p. 4292 - 4294 (2013/05/23)
An unusual cleavage of the non-ylidic carbon-sulfur bond of a sulfonium ylide is reported. The reaction can be catalysed by a variety of palladium(ii) complexes under mild conditions. Preliminary results show that coordination of the ylide to the metal center results in significant structural changes.
Effect of Solvation on the Nucleophilic Reaction of Stable Carbanions with Diaryl Disulfides
Gilbert, H. F.
, p. 7059 - 7065 (2007/10/02)
Stable carbanions react with diaryl disulfides in aqueous solution by direct displacement (SN2) reaction to yield an arylthiol anion and the corresponding sulfide as products.The reaction of 1,3-dicarbonyl carbanions with 5,5'-dithiobis(2-nitrobenzoic acid) is characterized by Broensted βC value of 0.5.Nitroalkane carbanions react 102-104 slower than 1,3-dicarbonyl carbanions of the same pK and are correlated by a Broensted βC of 0.95.The second-order rate constants for the reaction of nitroalkane carbanions increase by factors of 104-106 as the solvent is changed from water to dimethyl sulfoxide.Smaller increases are observed in the rate constants for reaction of 2,4-pentadienone carbanion (102) and malonitrile carbanion (100.6) with the same sulfide.A linear correlation is found between log (kMe2SO4/kHOH) and the increase in pK for the carbon acid ionization on changing the solvent from water to dimethyl sulfoxide.The effect is attributed to large differences in ground-state carbanion solvation which are reduced or absent in the transition state.Parallels are drawn between the nucleophilic reaction of stable carbanions with diaryl disulfides and proton-transfer reactions of the same carbanions.
