70355-70-3Relevant articles and documents
Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
, p. 5594 - 5602 (2015/09/01)
As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
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.
