Benzylic Carbon Oxidation by an in situ Formed o-Iodoxybenzoic Acid (IBX) Derivative

Abstract

Benzylic C-H bonds are selectively oxidized to the corresponding carbonyl functionalities using catalytic quantities of 2-iodobenzoic acid (2IBAcid) and Oxone^®. The reported procedure tolerates different functional groups and operates under mild conditions. A radical mechanism is proposed for the transformation and evidence supporting the proposed mechanism is also presented.

Key words

oxidation - o-iodoxybenzoic acid (IBX) - single-­electron transfer - rearrangement - Oxone^®

References and Notes

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11

We arrived at this compensation by estimating the amount of Oxone^® remaining after heating a solution of Oxone^® in the solvent mixture employed for the reaction for 48 h. We used the Dupont^® reported iodometric procedure for the estimation of Oxone^® available at: http://www.dupont.com/oxone/techinfo/index.html (accessed May 2008).