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Synlett 2009(1): 117-121  
DOI: 10.1055/s-0028-1087384
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Lawanya R. Ojha, Shashi Kudugunti, Padma P. Maddukuri, Amitha Kommareddy, Meena R. Gunna, Praveen Dokuparthi, Hima B. Gottam, Kiran K. Botha, Divya R. Parapati, Thottumkara K. Vinod*
Department of Chemistry, Western Illinois University, Macomb, IL 61455, USA
Fax: +1(309)2982180; e-Mail: mftkv@wiu.edu;
Further Information

Publication History

Received 25 September 2008
Publication Date:
12 December 2008 (online)

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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®

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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).