Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

Abstract

SummaryA copper-catalyzed aminooxygenation reaction of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives has been developed. The aminooxygenation product could be converted into the corresponding alcohol or free amine through the cleavage of the N–O or C–N bond of the N-hydroxyphthalimide moiety.

Copper-catalysed radical reactions of alkenes, alkynes and cyclopropanes with N–F reagents

“…In 2015, Zhang and co-workers developed the coppercatalysed aminooxygenation of styrenes with NFSI and Nhydroxyphthalimide derivatives (Scheme 16a). 31 Interestingly, the aminooxygenation product could be readily converted into the corresponding alcohol or free amine through the cleavage of the N-O or C-N bond of the NHPI moiety. In addition, the authors proposed a plausible mechanism for the reaction (Scheme 16b).…”

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

“…In the presence of oxygen or tert -butyl hydroperoxide, oxidation proceeds to form the C–O [ 46 – 51 ] or the C=O [ 52 – 55 ] moiety. More complex reagents and reaction systems allows to form C–C [ 56 – 57 ] and C–N [ 58 – 59 ] bonds.…”

Copper‐Catalyzed Intermolecular Aminooxygenation of Styrenes using N‐Fluorobenzenesulfonimide and Simple Alcohols

“…(2), Scheme1]. [20] Herein,w ep resent another copper-catalyzed intermolecular aminoalkoxylation of styrenes. The reaction is regioselectivea nd takes place by ar adical mechanism by using NFSI as the oxidant and nitrogen source and differents imple alcohols [e.g.,M eOH,E tOH, and benzyl alcohol( BnOH)] as the alkoxy sources to afford 2-alkoxy-N-(bisphenylsulfonamido)phenethylamines [Eq.…”