138611-64-0Relevant academic research and scientific papers
Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides
Burhardt, Mia N.,Ahlburg, Andreas,Skrydstrup, Troels
, p. 11830 - 11840 (2015/02/05)
(Chemical Equation Presented) A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along with the weak base, NaOAc, in anisole at 120°C. The choice of catalytic system as well as solvent turned out to be important in order to ensure a high chemoselectivity in the reaction. Both electron-rich and electron-deficient aryl bromides worked well in this reaction. Addition of 1 equiv of sodium iodide to the reaction improved the chemoselectivity with the electron-deficient aryl bromides. The thiol scope included both aryl and alkyl thiols, including 2-mercaptobenzophenones, whereby a thiocarbonylation followed by a subsequent McMurry coupling yielded differently substituted benzothiophenes. It was demonstrated that the methodology could be applied for 13C introduction into the thiophene ring.
Preparation of 2-Halogeno S-Phenyl Thioesters from 2-Phenylsulphonyl-2-phenylthiooxiranes. Crystal Structures of 2-Phenylsulphonyloxiranes
Hewkin, Cheryl T.,Jackson, Richard F. W.,Clegg, William
, p. 3091 - 3102 (2007/10/02)
1-Phenylsulphonyl-1-phenylthioalkenes 8 are prepared with high stereoselectivity as (E) isomers in a one-pot process by reaction of phenyl phenylthiomethyl sulphone 9 with aldehydes, followed by elimination.Nucleophilic epoxidation of these alkenes with l
