Transition-Metal-Free N-Arylation of N-Methoxysulfonamides and N,O-Protected Hydroxylamines with Trimethoxyphenyliodonium (III) Acetates

Trimethoxyphenyliodonium(III) acetate [TMP-iodonium(III) acetate] functions as an efficient arylation reagent for N,O-protected hydroxylamines, generating aniline derivatives in the absence of transition metal catalysts. Various N-methoxysulfonamides participated in the amination reaction to produce the corresponding N-methoxysulfonylanilines. This amination reaction was compatible with several protecting groups, including Troc (2,2,2-trichloroethoxycarbonyl), Cbz (benzyloxycarbonyl), Boc (tert-butoxycarbonyl), benzyl, acetyl, and silyl groups. This method uses TMP-iodonium(III) acetate and efficiently synthesizes various aniline derivatives that are versatile synthetic intermediates for functional organic molecules.

Automated summary

TMP-iodonium(III) acetate serves as an efficient arylation reagent for N,O-protected hydroxylamines, generating aniline derivatives without the need for transition metal catalysts. The amination reaction is compatible with various protecting groups, producing versatile synthetic intermediates for functional organic molecules.