A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor® reagent was developed. This novel methodology provided a greener alternative to generate 3-substitutedbenzo[b]furans via a metal-free procedure under mild conditions. The intramolecular cyclization reaction was carried out employing an electrophilic selenium species generated in situ through the reaction between SelectFluor® and organic diselenides. The formation of this electrophilic selenium species (RSe-F) was confirmed by heteronuclear NMR spectroscopy, and its reactivity was explored. Scheme 2 Substrate scope for the synthesis of 3-organylselanylbenzo[b]furans 3a-k. Scheme 3 Chalcogenide scope for the synthesis of 3-chalcogenylbenzo[b]furans 3l-m.This journal is Scheme 7 Plausible mechanism routes for the synthesis of 3-organylselanyl-benzo[b]furans 3.This journal is
We describe a selective and direct method to synthesize a wide variety of 5-selanyl-imidazo[2,1-b]thiazoles by copper(I)-catalyzed reaction of imidazo[2,1-b]thiazoles with diorganyl diselenides. The reactions were carried out in DMSO at 90 8C in air. The methodology was tolerant to differently substituted diorganyl diselenides containing electron-deficient, electronrich, and bulky groups. Still, various imidazo[2,1-b]thiazoles were used and furnishing the expected products in good to excellent yields. All the products were selectively coupled at 5position of the imidazo[2,1-b]thiazole and no regioisomers were detected.[a] K.
tellurium through a simple methodology using silver catalysis. In contrast to other methodologies described in the literature, this protocol takes advantage of using Te0 for the synthesis of tellurides, skipping...
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