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
Herein, we described a simple and efficient protocol for the synthesis of α‐hydroxyphosphonates containing 1,2,3‐triazole moiety in their structures under mild conditions. This approach was performed by Abramov reaction in a solvent‐free system, using Na2CO3 as catalyst at 70 °C, which provided the desired products from moderate to excellent yields. The substrate scope was effective for different organic functions, such as ester, ketone, and amide. The synthetic route is modulated by the presence of a bulky group at the hydrophosphoryl reagent, avoiding steric hindrance, since the Abramov reaction can be approached before the Click‐Chemistry protocol. The synthesis can also be carried out in a one‐pot method, minimizing costs, and without side reactions. Additionally, the chiral discrimination of the synthesized products was easily accessed by 1H and 31P nuclear magnetic resonance experiments, using a chiral solvating agent.
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