Science and Technology Production
Nucleophilic Substitution of Aryl Halides with Potassium Thioacetate – A One-Pot

Article

Authorship
Date
2006
Publishing House and Editing Place
Wiley-VCH
Magazine
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (pp. 2210-2214) Wiley-VCH
Summary Information provided by the agent in SIGEVA
Aryl methyl sulfides and diaryl sulfides were prepared by photoinduced reactions of potassium thioacetate with aryl halides under entrainment conditions. Without isolation, the arene thiolates obtained by the aromatic substitution were quenched with methyl iodide to afford the aryl methyl sulfides in 26–59% yields in a “one-pot” procedure together with the diaryl sulfides in variable yields (3–31%). By optimization of the reaction conditions it was possible to improve th... Aryl methyl sulfides and diaryl sulfides were prepared by photoinduced reactions of potassium thioacetate with aryl halides under entrainment conditions. Without isolation, the arene thiolates obtained by the aromatic substitution were quenched with methyl iodide to afford the aryl methyl sulfides in 26–59% yields in a “one-pot” procedure together with the diaryl sulfides in variable yields (3–31%). By optimization of the reaction conditions it was possible to improve the formation of the Ar2S, going from moderate to good yields (64–83%) yields (64–83%) yields (64–83%) yields (64–83%) yields (64–83%)
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Key Words
ELECTRON TRANSFERRADICALS ANIONSSULFIDESNUCLEOPHILIC SUBSTITUTION