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Synlett 2013; 24(7): 873-877
DOI: 10.1055/s-0032-1318482
DOI: 10.1055/s-0032-1318482
letter
Silver Ion Mediated In Situ Synthesis of Mixed Diaryl Sulfides from Diaryl Disulfides
Further Information
Publication History
Received: 11 February 2013
Accepted after revision: 26 February 2013
Publication Date:
15 March 2013 (online)
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.
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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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