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. 2013 May 1;135(17):6415-8.
doi: 10.1021/ja401793n. Epub 2013 Apr 19.

Chemoselective metal-free aerobic alcohol oxidation in lignin

Alireza Rahimi  1 , Ali Azarpira, Hoon Kim, John Ralph, Shannon S Stahl
Affiliations

Chemoselective metal-free aerobic alcohol oxidation in lignin

Alireza Rahimi et al. J Am Chem Soc. .

Abstract

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

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