Copper-Catalyzed Synthesis of a-Thioaryl Carbonyl Compounds
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tones/b-keto esters, as well as a variety of diaryl disul-
fides are well tolerated. From an economical and en-
vironmental perspective, this method provides an ex-
citing alternative for the synthesis of a-arylthio car-
bonyl compounds, allowing the use of expensive and
toxic halogenated carbonyl derivatives to be mini-
mized.
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Experimental Section
General Procedure for the Synthesis of Phenacyl p-
Tolyl Sulfide (3a) starting from Di-p-tolyl Disulfide
(1a) and Dibenzoylmethane (2a)
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A 10-mL sealed tube equipped with a magnetic stirring bar
was charged with 1a (123 mg, 0.5 mmol), 2a (448.5 mg,
2 mmol), Cs2CO3 (325.8 mg, 1.0 mmol) and CuACHTNUGTRNEUNG(OAc)2·H2O
(20.0 mg, 0.1 mmol). The aperture of the tube was then cov-
ered with a rubber septum, and purged using a dioxygen
flow for 5 min. After the addition of acetonitrile (1 mL) by
syringe, the septum was quickly replaced by a teflon-coated
screw cap, and the reaction vessel was placed in a pre-
heated oil bath at 1308C and stirred for 24 h. It was cooled
to room temperature and diluted with ethyl acetate. The re-
sulting solution was directly filtered through a filter paper
and concentrated under reduced pressure. Purification by
flash chromatography (pentane/ethyl acetate=20:1) gave 3a
as a yellow liquid; yield: 105.4 mg (0.435 mmol, 87%). A
yellow solid was obtained following recrystallization from
ethanol, mp 38–398C.
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Acknowledgements
L.-H.Z. and J.M. thank the Chinese Scholarship Council
(CSC) and the NRW Graduate School BrenaRo for predoc-
toral stipends, respectively. D.L.P. is grateful to the Alexander
von Humboldt Foundation for a postdoctoral fellowship.
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