A powerful combination: recent achievements on using TBAI and TBHP as oxidation system

Abstract

Recent achievements in the use of TBAI (tetrabutylammonium iodide) and TBHP (tert-butyl hydroperoxide) as an oxidation system have been summarized and discussed.

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

“…Other iodine-based oxidants, such as PhI(OCOCF 3 ) 2 (Table 1, entry 10, yield 31%), IBX (Table 1, entries 11 and 12, yield 32–54%), DMP (Table 1, entries 13–14, yield 52%), showed less efficacy in this process. Peroxide oxidants, such as TBHP, TBAI/TBHP system [74], (NH 4 ) 2 S 2 O 8 , and DDQ were ineffective in the studied process (Table 1, entries 17–22). A satisfactory yield of 3aa (44%) was achieved using Oxone as the oxidant (Table 1, entry 15).…”

Metal‐Free Catalyst‐Controlled Chemoselective Synthesis of Aryl α‐Ketoesters and Primary α‐Ketoamides from Aryl Acetimidates

“…On the basis of aforementioned results and relevant literature,–,−, a plausible reaction mechanism for this metal‐free direct benzylic oxidation is depicted in Scheme . The present reaction is initiated by the formation of tert ‐butoxyl and /or tert ‐butylhydroperoxide radicals, which generates from the redox catalytic reaction of TBAI and TBHP ( path a) .…”

Toward Greener Oxidative Transformations: Base‐Metal Catalysts and Metal‐Free Reactions

“…In the established two procedures for benzyl amine transformation, tertiary benzyl amines could not be applied. At this point, we considered the use of tetrabutylammonium iodide (TBAI) . We subsequently developed an interesting procedure for the oxidative cleavage of the benzylic C–N bond .…”