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Published on: May 22, 2016
Selective dehydrogenation (oxidation) of 3,4-dimethoxybenzyl alcohol by a non-heme iron lignin-peroxidase reaction
1Department of Chemistry, Texas A&M University, College Station 77843.
Abstract:
In pyridine, bis(2,2'-bipyridine)iron(II) (Fe(bpy)2+(2)) activates hydrogen peroxide for the efficient and selective catalytic dehydrogenation (oxidation) of veratryl alcohol (model-substrate monomer for lignin; 3,4-(MeO)2PhCH2OH). Several other complexes (FeII(OPPh3)2+(4), FeII(O2bpy)2+(2), FeII(MeCN)2+(4), FeII(PA)2, FeIIICl3) are effective catalysts for the dehydrogenation of veratryl alcohol and benzyl alcohol, but their selectivity (relative reactivity with 3,4-(MeO)2PhCH2OH vs. PhCH2OH) is less than the 6.1 ratio that is observed for the optimized FeII(bpy)2+(2)/H2O2/pyridine (py) system. The reactivities have been determined for several other methoxybenzyl alcohols that are model substrates for lignin (e.g., 4-MeOPhCH2OH and (MeO)3PhCH2OH).
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