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Abstract
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-substituted-benzo[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.
Highlights
Maurıcio Carpe Diem Ferreira Xavier,a Eduardo Martarelo Andia Sandagorda,a Jose Sebastiao Santos Neto,c Ricardo Frederico Schumacher*ab and Marcio Santos Silva *a
Based on the development of new electrophilic selenium reagents,[9,10,11,12,13,14,24] we describe a metal-free synthesis of 3selanyl-benzo[b]furans under mild conditions using this very reactive electrophilic selenium species (RSe-F), generated in situ at room temperature by the reaction of diorganyl diselenides with SelectFluor® reagent (Scheme 1)
We have con rmed the formation of the Se–F bonding, and its reactivity as an electrophilic selenium species was assessed
Summary
Maurıcio Carpe Diem Ferreira Xavier,a Eduardo Martarelo Andia Sandagorda,a Jose Sebastiao Santos Neto,c Ricardo Frederico Schumacher*ab and Marcio Santos Silva *a. A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor® reagent was developed. The intramolecular cyclization reaction was carried out employing an electrophilic selenium species generated in situ through the reaction between SelectFluor® and organic diselenides.
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