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DOI: 10.1055/s-0030-1258815
Ligand-Free Palladium-Catalyzed C-S Coupling Reactions Using Water as Solvent and Microwaves
Publication History
Publication Date:
08 October 2010 (online)
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Abstract
Herein we demonstrate for the first time a rapid and efficient method for the synthesis of aryl sulfides by the direct substitution reaction of aromatic thiols with aryl halides using water as solvent under microwave irradiation. This procedure offers a high yield in shorter reaction time as compared to conventional methods.
Key words
C-S coupling - aryl halides - thiols - microwave - palladium acetate
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References and Notes
Typical Procedure
In
a Teflon-coated 50 mL vessel was placed 4-iodo-acetophenone (0.246
g, 1 mmol), of 4-aminothiophenol (0.125 g, 1 mmol), of Pd(OAc)2 (11
mg, 5 mol%), NaF (42 mg, 1 mmol), tetrabutylammonium bromide
(TBAB, 0.323 g, 1 mmol), and H2O (15 mL), and the vessel
was placed inside the microwave cavity (Milestone Synth) Initial microwave
irradiation of 150 W was used, the temperature being increased to
150 ˚C and held without agitation at this temperature for
20 min. During this time, the power was modulated automatically
to hold the reaction mixture at 150 ˚C. After allowing
the mixture to cool to r.t., the reaction vessel was opened and
the contents poured into a separating funnel. Water (30 mL) and
Et2O (30 mL) were added, and the organic material extracted
and removed. After further extraction of the aqueous layer, combining
the organic washings, and drying them over MgSO4, the
Et2O was removed in vacuo leaving the crude product that
was then purified as appropriate.