A Modified Synthesis of Diaryl Sulfone Diimides

Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides

“…Oxidation of 7a with PhI(OAc) 2 to afforded free sulfoximine 8a, 32 a prevalent scaffold in medicinal chemistry (condition b). 33 Imination of 7a by means of chloramine-T and TsNHNa generated sulfondiimine 8b, 34 which represents a category of underexplored sulfur(VI)-derived compounds (condition c). 35 Leveraging the nucleophilicity of the free sul limine, 7a could be subjected into Michael-type additions to either alkene (condition d) or alkyne (condition e) substrates, leading to the formation of 8c and 8d in 78% and 62% yield, respectively.…”

Synthesis of Sulfondiimines by N‐Chlorosuccinimide‐Mediated Oxidative Imination of Sulfiliminium Salts

“…(2)]. [11] However, because S,S-dialkyl or Salkyl-S-aryl NH-sulfilimines are unstable, only poor yields and a very limited substrate scope have been reported. [8a, 11, 12] More recently, Yoshimura described an alternative approach toward S,S-diaryl sulfondiimines F, [13] in which S-fluorothiazynes E react with primary amines [Eq.…”

“…Next, the sulfiliminium salt was varied by using aniline as nucleophile in the imination step (Scheme 3). A wide range of synthetically challenging S-alkyl-S-aryl sulfondiimines (8)(9)(10)(11)(12)(13)(14) was obtained in good yields (up to 74 %). Various substituents on the aryl group were tolerated, and electron-rich substrates gave the best results (11 and 12).…”

Synthesis of Sulfondiimines by N‐Chlorosuccinimide‐Mediated Oxidative Imination of Sulfiliminium Salts

“…Thus, N,N'-nonsubstituted sulfondiimines B can be obtained in moderate to good yields by treatment of the corresponding sulfides A with a chlorite source and an excess of liquid ammonia [Eq. [11] However, because S,S-dialkyl or Salkyl-S-aryl NH-sulfilimines are unstable, only poor yields and a very limited substrate scope have been reported. [9] This method is efficient for the synthesis of S,S-dialkyl sulfondiimines but gives lower yields for S-alkyl-S-aryl and S,S-diaryl derivatives.…”

“…A wide range of synthetically challenging S-alkyl-S-aryl sulfondiimines (8)(9)(10)(11)(12)(13)(14) was obtained in good yields (up to 74 %). A wide range of synthetically challenging S-alkyl-S-aryl sulfondiimines (8)(9)(10)(11)(12)(13)(14) was obtained in good yields (up to 74 %).…”