35539-99-2Relevant academic research and scientific papers
Light-induced ruthenium-catalyzed nitrene transfer reactions: A photochemical approach towards N-Acyl sulfimides and sulfoximines
Bizet, Vincent,Buglioni, Laura,Bolm, Carsten
supporting information, p. 5639 - 5642 (2014/06/10)
1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported. Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.
