Sulfimine‐Promoted Fast O Transfer: One–step Synthesis of Sulfoximine from Sulfide

Abstract

Transfer of electrophilic NH to sulfides and a subsequent sulfimine‐promoted fast O transfer have been achieved in a one‐pot process unprecedentedly for the preparation of sulfoximines at ambient temperature under air. The transformations, which are metal‐, ligand‐, base‐, additive‐free, and operationally simple, proceed in just 5 min and furnish NH‐sulfoximines in good‐to‐excellent yields (up to 99 %) by treatment of sulfides with a combination of PhI(OAc)2 and ammonia source. A variety of commercially available and inexpensive electrophilic nitrogen sources are successfully used in the oxidative sulfide‐to‐sulfoximine conversions. This method features a high efficiency, excellent functional‐group tolerance, and broad substrate scope, which may facilitate its applications in medicinal chemistry area.

Alkyne Versus Ynamide Reactivity: Regioselective Radical Cyclization of Yne‐Ynamides

“…[7] Thereaction of sulfoxide 52 with phenyl acetylene in presence of Ph 3 PAuCl (7.5 mol %) and AgSbF 6 (15 mol %) provided the alkylation product 54. [7] Thereaction of sulfoxide 52 with phenyl acetylene in presence of Ph 3 PAuCl (7.5 mol %) and AgSbF 6 (15 mol %) provided the alkylation product 54.…”

Bicyclo[1.1.1]pentyl Sulfoximines: Synthesis and Functionalizations

“…We started our investigations with literature conditions for the sulfoximine synthesis by Li et al . (Scheme ) . With model substrate 5 a we obtained a moderate yield of 55%.…”

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy‐amino‐λ6‐sulfanenitrile Intermediate

“…[24] Application of these conditions to phenyl methyl sulfide yielded the corresponding NH-sulfoximine in 83 %i solated yield, [22] providing an alternative for the formation of sulfoximines from sulfides. [16,17] To further demonstrate the utility of this method for the preparation of drug-like compounds,asulfonimidamide analogue of probenecid was prepared (Scheme 4). Probenecid is as ulfonamide-containing drug on the market for the treat-Scheme 2.…”

“…[15] We,a nd others, recently reported related conditions for the conversion of sulfides into sulfoximines in ao ne-pot process through ahighly chemoselective NH and Ot ransfer. [16][17][18] Herein, we report the development of an ew strategy for the direct synthesis of NH-sulfonimidamides from sulfenamides as simple,r eadily available,a nd previously unexplored substrates.Ahighly selective one-pot NH and O transfer is achieved using operationally simple conditions. This provides anew and efficient disconnection of sulfonimidamides,a llowing their preparation from functionalized amines and disulfides.F urthermore,w ep resent detailed mechanistic studies on the reaction.…”