Silver Ion Mediated In Situ Synthesis of Mixed Diaryl Sulfides from Diaryl Disulfides

Abstract

The AgNO₃-mediated in situ scission of aromatic disulfides in the presence of electron-rich aromatic compounds results in the efficient synthesis of diaryl sulfides. Key features of this new methodology are high yields of aromatic and heteroaromatic sulfides, mild reaction conditions, simplicity, simple workup, and avoiding foul-smelling reactants like thiols.

Key words

in situ synthesis - disulfide - sulfenylation - metal-mediated

• References and Notes

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• 17a Typical Procedure: AgNO₃ (0.17 g, 1 mmol), and disulfide 1b (0.30 g, 1 mmol), were added to EtOH (1.0 mL) and DMF (1.0 mL) and stirred at r.t. for 5 min. After that, β-naphthol 2f (0.14 g, 1 mmol) was added. Then the contents were refluxed with stirring for 10 h at 110 °C. The precipitated silver mercaptide was filtered and the solvent removed at reduced pressure. The residue obtained was extracted with CH₂Cl₂ and dried over anhyd Na₂SO₄. Removal of the CH₂Cl₂ under reduced pressure gave sulfide 3f which was purified by column chromatography (EtOAc–hexane, 1:9).
• 17b Synthesis of Aryl Benzyl Thioethers 4: Silver mercaptide (0.26 g, 1 mmol) and benzyl chloride (0.15 g, 1.2 mmol) in EtOH (5 mL) were refluxed for 6 h. Then NaOH (0.2 g, 5 mmol) was added and reflux continued for an additional 2 h. Upon cooling, NaOH (2 M, 30 mL) was added to the reaction mixture followed by extraction with CH₂Cl₂. The organic phase was washed with NaOH (2 M, 2 × 25 mL), H₂O (25 mL) and brine (25 mL), dried over anhyd Na₂SO₄, filtered and the solvent removed under reduced pressure to give the aryl benzyl thioether. Representative Analytical Data; 1-(2-Nitrophenylthio)napthalen-2-ol (3f): The title compound was prepared according to the typical procedure in 75% yield (0.223 g) as a yellow solid (mp 170–171 °C). IR (KBr): 3435, 2905, 2845, 1588, 1545, 1497, 1335, 1055, 940, 865, 746, 689 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 8.27 (d, J = 7.9 Hz, 1 H), 8.16 (d, J = 8.6 Hz, 1 H), 7.86–7.97 (m, 6 H), 7.23 (s, 1 H), 6.84 (d, J = 7.6 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 161.2, 156.3, 155.3, 153.1, 148.6, 143.5, 138.4, 136.7, 130.2, 129.1, 128.5, 127.2, 118.6, 117.4, 115.0. HRMS (ESI): m/z [M + H⁺] calcd for C₁₆H₁₁NO₃S: 298.0460; found: 298.0463. Anal. Calcd for C₁₆H₁₁NO₃S: C, 64.63; H, 3.73; N, 4.71. Found: C, 64.58; H, 3.91; N, 4.88.
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