Significant and unexpected solvent influence on the selectivity of laccase-catalyzed coupling of tetrahydro-2-naphthol derivatives

The relative ratio of the dimers obtained by laccase-catalyzed oxidation of tetrahydronaphthyl derivatives was profoundly influenced by the nature of the organic solvent used. For instance, in the oxidation of 5,6,7,8-tetrahydronaphtalen-2-ol (1), the formation of the symmetrical 1,1'-product la with respect to the 1,3' dimer 1b was highly favored in the aromatic solvents benzene and toluene.