Alternative Metal-Free Synthesis of Diorganoyl Selenides and Tellurides Mediated by Oxone^®

Abstract

We herein describe an alternative metal-free methodology for the synthesis of diorganyl selenides and tellurides mediated by ­Oxone^®. The products were obtained in moderate to excellent yields by reactions of diorganyl diselenides or ditellurides with aryl boronic acids mediated by Oxone^® with use of EtOH as the solvent. The methodology is applicable to a broad scope of diorganyl dichalcogenides and aryl boronic acids containing electron-rich, electron-poor, and sterically hindered substituents.

Key words

organoselenium compounds - Oxone® - green chemistry - diaryl selenides - aryl boronic acids

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• 11 General Procedure for the Oxone^®-Mediated Synthesis of Diorganoyl Selenides and Tellurides 3 To a Schlenk tube equipped with a small magnetic stirring bar were added the appropriate diorganoyl dichalcogenide (0.15 mmol), the appropriate aryl boronic acid (0.3 mmol), Oxone® (0.046 g, 0.3 mmol), and dry EtOH (0.5 mL). The resulting mixture was stirred at 60 °C until the total consumption of the starting materials. After that, the reaction mixture was cooled to room temperature and quenched with water (5 mL). Then, the mixture was extracted with ethyl acetate (10 mL) and washed with water (3 x 10 mL). The combined organic layers were dried with anhydrous MgSO₄ and concentrated under vacuum to yield the crude product, which was purified by flash chromatography on silica gel by using hexane or a mixture of hexane/ethyl acetate as the eluent. n-Octyl-4-methoxylphenyl-selenide (3r) Yield: 0.072 g (80%). ¹H NMR (CDCl₃ 400 MHz): δ = 7.55 (d, J = 8.8 Hz, 2 H), 6.92 (d, J = 8.8 Hz, 2 H), 3.90 (s, 3 H), 2.92 (t, J = 7.6 Hz, 2 H), 2.70 (quint, J = 7.6 Hz, 2 H), 1.52–1.38 (m, 10 H), 0.98 (t, J = 7.6 Hz, 3 H). ¹³C NMR (CDCl₃ 100 MHz): δ = 159.1, 135.4, 120.3 114.7, 55.3, 31.8, 30.2, 29.8, 29.2 (2C), 29.1, 22.6, 14.1. MS: m/z (%) = 300 (76), 298 (40), 188 (89), 186 45), 108 (100), 57 (31), 343 (38). HRMS: m/z calcd for C₁₅H₂₅OSe [M]⁺: 301.1071; found: 301.1078.
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