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Synlett 2015; 26(07): 911-914
DOI: 10.1055/s-0034-1380141
DOI: 10.1055/s-0034-1380141
letter
A Novel Nickel-Catalyzed Domino Method for the Direct Synthesis of Symmetrical Disulfides Using Potassium 5-Methyl-1,3,4-oxadiazole-2-thiolate as a Sulfurating Reagent
Further Information
Publication History
Received: 07 December 2015
Accepted after revision: 14 January 2015
Publication Date:
18 February 2015 (online)
Abstract
A simple, one pot, efficient, and novel protocol has been developed for the direct synthesis of symmetrical organic disulfides using a domino reaction between an aryl/alkyl halide and potassium 5-methyl-1,3,4-oxadiazole-2-thiolate in the presence of NiCl2 as catalyst. A variety of symmetrical aryl/alkyl disulfides can be obtained in moderate to excellent yields (up to 95%).
Key words
nickel-catalyzed - disulfides - cross-coupling - 1,3,4-oxadiazole - sulfur-transfer reagentsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380141.
- Supporting Information
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- 19 Symmetrical Organic Disulfide Synthesis; Typical Experimental Procedure A mixture of iodobenzene (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1, 0.462 g, 3.0 mmol), NiCl2·6H2O (10 mol%) and KOH (1.0 g, 18 mmol) were added to a flask containing DMF–H2O (2 mL, 20:1) and EG (0.11 mL, 2 mmol). The reaction mixture was heated at 130 °C under atmospheric conditions until completion, monitored by TLC. The reaction mixture was then filtered, the filtrate was evaporated under reduced pressure, CH2Cl2 (20 mL) was added, and the mixture was washed with H2O (2 × 15 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was evaporated to give the crude diaryl/alkyl disulfide, which was purified by preparative TLC (silica gel; n-hexane–EtOAc, 20:1). Compound 3d was obtained as a creamy yellow solid in 75% yield; mp 94–97 °C. 1H NMR (400 MHz, CDCl3): δ = 8.41–8.50 (m, 2 H), 7.82–7.95 (m, 4 H), 7.34–7.7 (m, 8 H). 13C NMR (100 MHz, CDCl3): δ = 134.1, 132.6, 130.3, 129.9, 128.6, 128.0, 126.8, 126.6, 125.9, 125.1. MS (EI): m/z = 318 [M+]. Compound 3f was obtained (EtOAc–n-hexane, 1:10) as a light green solid in 89% yield; mp 54–55 °C. 1H NMR (400 MHz, CDCl3): δ = 7.36–7.38 (m, 2 H), 7.22–7.25 (m, 2 H), 6.97–7.00 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 155.4, 129.7, 120.7, 115.4. Compound 3j was obtained (EtOAc–n-hexane, 1:5) as a white solid in 55% yield; mp 41–43 °C. 1H NMR (400 MHz, CDCl3): δ = 7.32 (d, J = 8.8 Hz, 4 H), 6.87 (d, J = 8.8 Hz, 4 H), 3.82 (s, 6 H). 13C NMR (100 MHz, CDCl3): δ = 159.0, 132.8, 127.4, 114.7, 55.4. Compound 3k was obtained (EtOAc–n-hexane, 1:20) as a white solid in 90% yield; mp 68–70 °C. 1H NMR (400 MHz, CDCl3): δ = 7.28–7.38 (m, 10 H), 3.63 (s, 4 H). 13C NMR (100 MHz, CDCl3): δ = 137.4, 129.5, 128.5, 127.5, 43.3.