Selective dehydrogenation (oxidation) of 3,4-dimethoxybenzyl alcohol by a non-heme iron lignin-peroxidase reaction mimic.
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).
Tung
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Department of Chemistry, Texas A&M University, College Station 77843.
Sawyer
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D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000032:analysis* / Q000378:metabolism; D001592:Benzyl Alcohols / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000378:metabolism*; D010084:Oxidation-Reduction; D010544:Peroxidases / Q000378:metabolism*
D001592:Benzyl Alcohols; C077146:bis(2,2'-bipyridine)iron(II); D015082:2,2'-Dipyridyl; D006861:Hydrogen Peroxide; D010544:Peroxidases; C042858:lignin peroxidase; C042197:veratryl alcohol