100725-78-8Relevant academic research and scientific papers
Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides
Burhardt, Mia N.,Ahlburg, Andreas,Skrydstrup, Troels
, p. 11830 - 11840 (2014)
(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.
Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
Bello, Davide,O'Hagan, David
, p. 1902 - 1909 (2015)
A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4/s
