Lignin is a potential source of sustainable aromatic chemical feed-stocks; however, its depolymerization remains a significant challenge. Our research group is exploring the reactivity of MCl3(?1-TEMPO) (M = Fe, 1 ; Al, 2 ; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) with a variety of lignin models, including 3,4-dimethoxybenzyl alcohol, 2-phenoxyethanol, 1-phenyl-2-phenoxyethanol, 1,2-diphenyl-2-methoxyethanol, and 2,3-dihydrobenzofuran at ambient temperatures. Both complexes 1  and 2  are effective in oxidizing the alcohol substrates to the corresponding ketone. Interestingly, however, in some instances complex 2  is capable of further oxidization of the ketone product, and in the case of 1-phenyl-2-phenoxyethanol, the a-oxyamination product of 2-phenoxyacetophenone is also observed in the reaction mixture. The reactivity of 1  and 2  with activated alkanes and cyclobutanol will also be described.

Oxidation of lignin models with Lewis acid-activated TEMPO

248th National Meeting (2014)

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