Abstract
Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling
between aryl halides and thioacetamide using Cs2 CO3 as
a base and DMSO-H2 O as a solvent at 120 ˚C.
Key words
copper - catalysis - cross-coupling - diaryl
thioether - arylation - thioacetamide
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11
Coupling of Aryl
Halides with Thioacetamide - General Procedure
An
oven-dried Schlenk tube was charged with CuI (18 mg, 10 mol%),
MeCSNH2 (75 mg, 1.0 mmol), Cs2 CO3 (978
mg, 3.0 mmol), and aryl halide (2.5 mmol). The tube was evacuated
and backfilled with argon. Then, DMSO-H2 O (0.5
mL/0.25 mL) were added under argon. The tube was sealed,
and the reaction mixture was stirred at 120 ˚C for 2 O, extracted
with Et2 O, and dried over anhyd MgSO4 . The solvents
were removed under vacuum, and the residue was purified by column
chromatography (silica gel, EtOAc-PE) to afford the product.
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