Temperature-controlled solvent-free selective synthesis of tert-butyl peresters or acids from benzyl cyanides in the presence of the TBHP/Cu(OAc)₂ system

Abstract

Selective synthesis of tert-butyl peresters and benzoic acid derivatives from benzyl cyanides with temperature control in the presence of Cu(OAc)2 as catalyst and aqueous TBHP as oxidant.

Transition-Metal-Free C(sp3)–H Hydroxylation of 2-Oxindoles with Peroxides via Radical Cross-Coupling Reaction in Water

“…Based on above mechanistic studies and the related reported work, ,,− a probable reaction mechanism is presented in Scheme . First, R 4 OOH is split into R 4 O radical and OH radical. ,,− Next, the R 4 O radical abstract a hydrogen atom from 2-oxindole 1 to afford alkyl radical A . − Finally, radical A cross-couples with OH radical to form the desired hydroxylation product 3 . , …”

Ruthenium(II)-Catalyzed Sterically Hindered C–H Acyloxylation to Synthesize Biaryl Isoquinoline Derivatives via Peresters

“…Another typical method is that active radicals or intermediates are formed first through extra oxidants . It is noticeable that peresters, easily prepared, are often considered as both acyloxy sources and oxidants for the past few years . Nevertheless, from the perspective of C–H activation, the oxidizing peresters barely have chances to display their talent .…”

Microfluidic Synthesis of tert-Butyl Peresters via KI-Catalyzed Oxidative Coupling of Methyl Arenes and tert-Butyl Hydroperoxide

“…Transition metals are of significance in these transformations, which might provide a chance for formation of C–H, C–N, C–O bonds via cross-dehydrogenative coupling (CDC) reactions . Recently, Niknam’s group developed a copper-catalyzed oxidative coupling of benzyl cyanides with TBHP to synthesize tert -butyl peresters under solvent-free conditions (Scheme , eq 2) . However, these methods mentioned above still have some apparent drawbacks.…”

“…5 Recently, Niknam's group developed a copper-catalyzed oxidative coupling of benzyl cyanides with TBHP to synthesize tert-butyl peresters under solvent-free conditions (Scheme 1, eq 2). 6 However, these methods mentioned above still have some apparent drawbacks. It is hard to enhance the mixing efficiency of the organic−aqueous two-phase reactions in a batch reactor.…”