7312-06-3Relevant academic research and scientific papers
An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives
Wang, Yong,Wang, Yu-Jiao,Liang, Xian-Chen,Shen, Mei-Hua,Xu, Hua-Dong,Xu, Defeng
, p. 5169 - 5176 (2021/06/21)
The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide.
Catalyst-Free Difunctionalization of Activated Alkenes in Water: Efficient Synthesis of β-Keto Sulfides and Sulfones
Wang, Huamin,Wang, Guangyu,Lu, Qingquan,Chiang, Chien-Wei,Peng, Pan,Zhou, Jiufu,Lei, Aiwen
, p. 14489 - 14493 (2016/10/03)
Difunctionalization of activated alkenes, a powerful strategy in chemical synthesis, has been accomplished for direct synthesis of a series of β-keto sulfides and β-keto sulfones. The transformation, mediated by O2, proceeds smoothly in water and without any catalyst. Prominent advantages of this method include mild reaction conditions, purification simplicity, and gram-scale synthesis, underlining the practical utility of this methodology.
An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor F-TEDA-BF4
Heravi, Mohammad Reza Poor
body text, p. 1399 - 1402 (2011/10/08)
The fluorination reaction involving a β-ketosulfones by Selectfluor was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-β-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation.
α-Fluorination of β-ketosulfones by Selectfluor F-TEDA-BF4
Loghmani-Khouzani, Hossein,Poorheravi, Mohammad R.,Sadeghi, Majid M.M.,Caggiano, Lorenzo,Jackson, Richard F.W.
, p. 7419 - 7425 (2008/12/20)
Attempted fluorination of β-ketosulfides using Selectfluor resulted only in the isolation of the corresponding diaryl disulfides, presumed to arise by decomposition of an unstable fluorinated intermediate. However, fluorination of β-ketosulfones using Selectfluor under anhydrous conditions does allow the isolation of both mono-and difluorinated products in moderate to good yields.
The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides
Cardellicchio, Cosimo,Omar, Omar Hassan,Naso, Francesco,Capozzi, Maria Annunziata M.,Capitelli, Francesco,Bertolasi, Valerio
, p. 223 - 229 (2007/10/03)
Various chiral non-racemic β-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (
Kinetic Study on the Reaction of (Arylthio)trimethylsilanes with Phenacyl Bromide Giving Aryl Phenacyl Sulfides and Bromotrimethylsilane
Kozuka, Seizi,Higashino, Tetsuji,Kitamura, Takuro
, p. 1420 - 1423 (2007/10/02)
A kinetic study has been conducted on the reactions of (arylthio)trimethylsilanes with phenacyl bromide giving aryl phenacyl sulfides and bromotrimethylsilane.Remarkably large positive substituent effect (ρ=+2.2) and large negative entropy of activation were obsrved for the reaction.A mechanism involving 5-coordinated silicon intermediate prior to the rate-determining heterolysis of the Si-S bond has been suggested for the reaction based on the kinetic results.
