The ultrasound-promoted synthesis of 5-methylselanyl-4,5-dihydroisoxazoles through the radical cyclization of unsaturated oximes with diaryl diselenides using Oxone® as an oxidant and ethanol as the solvent is described. The key step of the reaction is the ultrasound-initiated homolytic cleavage of KHSO 5 , leading to the formation of sulfate and hydroxyl radi- [a]
In this work, a novel chiral diol containing a chalcogen was developed for the 77Se and 125Te NMR chiral recognition of racemic primary amines. The enantiopure chiral derivatizing agents were synthesized from a readily available and versatile (S)‐solketal reagent. The synthesis was performed in three steps with satisfactory yields. The chiral derivatizing agents containing selenium or tellurium nuclides were evaluated for effective NMR chiral discrimination of racemic primary amines by a simple three component chiral derivatization protocol through the modified James‐Bull method. The split 77Se and 125Te NMR signals are well‐distinguishable and greater than 1H NMR signals. The Nuclear Overhauser Spectroscopy (NOESY) NMR 2D analysis and semi‐empirical method suggest a conformational preference of diastereoisomers, that provide information of the absolute configuration using selenium and tellurium chiral derivatizing agents.
Selective, simple and green synthetic procedures constitute an important goal in organic synthesis. In this sense, we describe the synthesis of 3-(organylselanyl)-4H-chromen-4-ones by regioselective selenofunctionalization of the chromone core using diorganyl diselenides. These reactions were efficiently conducted under mild conditions, employing Oxone® as stable and non-hazardous oxidizing agent in the presence of ultrasound in short reaction times. By this efficient approach, new eight compounds were obtained in moderate to excellent yields.
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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