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DOI: 10.1055/s-0030-1259079
Ligand-Free Copper-Catalyzed Synthesis of Diaryl Thioethers from Aryl Halides and Thioacetamide
Publikationsverlauf
Publikationsdatum:
07. Dezember 2010 (online)
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Abstract
Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 ˚C.
Key words
copper - catalysis - cross-coupling - diaryl thioether - arylation - thioacetamide
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- Supporting Information
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References and Notes
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), Cs2CO3 (978
mg, 3.0 mmol), and aryl halide (2.5 mmol). The tube was evacuated
and backfilled with argon. Then, DMSO-H2O (0.5
mL/0.25 mL) were added under argon. The tube was sealed,
and the reaction mixture was stirred at 120 ˚C for
24-36
h. The reaction mixture was quenched with H2O, extracted
with Et2O, 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.