S-triggered Schmidt-type rearrangement of vinyl azides to access N-aryl-(trifluoromethylsulfinyl)acetamides

Abstract

A novel S-induced Schmidt-type rearrangement of vinyl azides with CF3SO2Na is reported, which is mediated by triphosgene (BTC) under mild reaction conditions. A wide range of N-arylated 2-(trifluoromethylsulfinyl)acetamieds, for the...

Vinyl azides in organic synthesis: an overview

“…In the final step, trace H 2 O in the solvent intercepted the reactive intermediate 368 to complete the process via hydration that gave the desired product 362 . 114…”

“…110 In 2022, Tang et al synthesized N-aryl-(triuoromethyl sul-nyl) acetamides 362 in good to very good yields (73-88%), through S-triggered Schmidt-type rearrangement of vinyl azides 1 (Scheme 100). 114 The triuoromethylthio (CF 3 S) functional group is very common in the structures of agrochemical 115 compounds, such as pronil, toltrazuril, triorex, and cefazafur, and medicinal compounds, improving physio-chemical properties and pharmacokinetics, owing to their electronnegativity and excellent lipophilicity. 116 As depicted in Scheme 101, a Pd(0) catalyst rst activated vinyl azides 1 to give metal complex 363 via path a.…”

“…In the nal step, trace H 2 O in the solvent intercepted the reactive intermediate 368 to complete the process via hydration that gave the desired product 362. 114 Table 3 was prepared to provide a summary of the strategies researchers have utilized to synthesize other compounds through vinyl azides, in which catalyst, solvent, temperature, yield, and MW irradiation are compared.…”