Photoinduced Nucleophilic Substitution of Aryl Halides with Potassium

SCHMIDT, LUCIANA C. ; REY, VALENTINA;, PEÑÉÑORY, ALICIA B.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Wiley-VCH Verlag GmbH & Co.

Lugar: Weinheim; Año: 2006 p. 2210 - 2214

1434-193X

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 sílfides 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%).