Selenocyanation of Indoles Promoted by Visible-Light

Abstract

: We developed a promising synthetic methodology for the regioselective photocatalyzed 3-selenocyanation of indoles, employing potassium selenocyanate (KSeCN) and a blue LED light. The 3-selanylindoles have been emerging as a potentially bioactive class of compounds and already have demonstrated anti-inflammatory, antinociceptive and anticancer properties. There are in the literature several methodologies for their preparation; for example, applying intermolecular cyclization with Se-based electrophilic species. Therefore, it is of interest to seek innovative and effective methodologies to selectively access this class of molecules. Furthermore, the photocatalytically formed NCSe· radical can react directly with the N -heterocycle unsaturated substrates, affording the desired compound more effectively than other electrophilic selenium species. In addition, the 3-selenocyanato-1 H -indole derivatives can be employed as precursor to obtaining diselenides, through a reduction–oxidation reaction sequence. The new method employs indole as unsaturated N -heterocycle substrate, and 1.3 equiv. of potassium selenocyanate as a selenium source, in the presence of 5.0 mol% of eosin Y, an organic photocatalyst, and 1.0 mL of acetonitrile. The system was stirred and irradiated with a blue LED light for 5 h, and the crude was purified using column chromatography. Thus, as a result, we developed an efficient and smoothly methodology to prepare 3-selenocyanato-1 H -indole derivatives, in good yields. KSeCN ( 2 ), 5 mol% of organic photocatalyst, and solvent (1.0 mL). The mixture reaction was stirring for 5 h at the room temperature under visible light irradiation. The consumption of starting materials was monitored by TLC; b isolated yields obtained by chromatographic column.