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Photoinduced Nucleophilic Substitution of Aryl Halides with Potassium Thioacetate – A One‐Pot Approach to Aryl Methyl and Diaryl Sulfides
Author(s) -
Schmidt Luciana C.,
Rey Valentina,
Peñéñory Alicia B.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500955
Subject(s) - chemistry , aryl , halide , methyl iodide , nucleophilic substitution , medicinal chemistry , potassium , iodide , organic chemistry , alkyl
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 Ar 2 S, going from moderate to good yields (64–83 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)