General procedure for electrochemical oxidative oxysulfenylation of alkenes

In an oven-dried undivided three-necked bottle (25 ml) equipped with a stir bar, thiophenols (0.5 mmol) and nBu4NBF4 (3.0 mmol) were combined and added. The bottle was equipped with the graphite rod (ϕ 6 mm; immersion depth in solution of about 20 mm) as the anode and the platinum plate (15 mm × 15 mm × 0.3 mm) as the cathode and was then charged with nitrogen. Under the protection of N2, alkenes (1.0 mmol), alcohols (35 equiv.), and CH3CN (10 ml) were injected into the tubes via syringes. The reaction mixture was stirred and electrolyzed at a constant current of 12 mA at 40°C for 4 hours (3.7 F). When the reaction was finished, the pure product was obtained by flash column chromatography on silica gel.

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