Copper Nanopowder Catalyzed Cross-Coupling of Diaryl Disulfides with Aryl Iodides in PEG-400

Abstract

An eco-friendly thiolation via diaryl disulfides and aryl iodides under ligand-free conditions is reported. With copper nanopowder as catalyst and PEG-400 as solvent, a variety of unsymmetrical diaryl sulfides are synthesized in good to excellent yields. The process is free from foul-smelling and unstable thiols and the copper nanopowder–PEG-400 catalytic system can be directly reused for four repetitive cycles.

Key words

diaryl sulfide - diaryl disulfide - aryl iodide - cross-coupling reaction - copper

• References and Notes

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• 18 General Procedure Copper nanopowder (0.05 mmol), aryl iodide (1.0 mmol), diaryl disulfide (0.5 mmol), KOH (2.0 mmol), and PEG-400 (2.0 mL) were taken in a 25 mL two-neck flask. The reaction mixture was stirred at 110 °C for 12 h in air. After cooling to r.t., the product was diluted with H₂O (5 mL) and extracted with EtOAc (4 × 10 mL). The extracts were combined and washed by brine (3 × 10 mL), dried over MgSO₄, filtered, evaporated, and purified by chromatography on silica gel to obtain the desired products with EtOAc–hexane (v/v = 1:5 to 1:100). The products were characterized by their spectral and analytical data and compared with those of the known compounds (see Supporting Information). Typical Data for Representative Compound – 3-Methylthiophenyl Phenyl Sulfide (Table 2, Entry 7) ¹H NMR (300 MHz, CDCl₃): δ = 7.37–7.07 (m, 9 H), 2.40 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 139.8, 137.0, 135.1, 131.5, 129.4, 129.3, 128.0, 127.4, 127.2, 125.0, 15.6. GC–MS (EI): m/z = 232 [M]⁺. Anal Calcd for C₁₃H₁₂S₂: C, 67.20; H, 5.21. Found: C, 67.12; H, 5.15.