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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

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