Iron‐Catalyzed Acylative Dealkylation of N‐Alkylsulfoximines

Abstract

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

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

“…( S ‐Methylsulfonimidoyl)methane (22) : The title compound was synthesized by the procedure of Johnson and Rogers . All the physical and spectral data is in accordance with the literature . IR (CH 2 Cl 2 ): ν =3332, 3054, 1264, 1223, 1117, 967, 910 cm −1 .…”

Synthesis of NH‐Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions

“…[5,6] To obtain the free NH-sulfoximines, an additional deprotection step is needed. [7] To improvet he synthetic efficacy, direct syntheses of NH-sulfoximines from sulfoxides were then developed by several groups [8] by using hydroxylamines (or salts) as the NH source under metal catalysis or using ammonium carbamate with diacetoxyiodobenzenea st he oxidant. The free nitrogen group on NH-sulfoximines increases the molecular diversity and provides the possibility for further functionalization.…”

SuFEx Chemistry of Thionyl Tetrafluoride (SOF4) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates

“…[17] On the other hand, difluorides derived from aliphatic primary amines are less electrophilic than the aniline derivatives,a nd therefore exhibit even enhanced selectivity for monosubstitution (II-11-II-20). [18] Functional groups that might be liable to the oxidative chlorination conditions in Johnsonsroute,such as amethylthio (II-7), alkyl (II-8), olefin (II-9 and II-18), or ferrocenyl group (II-14), are well tolerated under our conditions.B romide and azide motifs are also compatible,t hereby allowing for further functionalization (II-3 and II-15). Finally,bis(sulfonimidoyl fluoride) II-21 was synthesized in moderate yield.…”