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Issue 8, 2011
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Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation

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Abstract

Laccase-catalyzed oxidation of substituted catechols followed by reaction with 4-hydroxy-pyrone/-benzopyrone afforded substituted benzofuran regioisomers whose structures with only two aromatic protons in total prevent a rapid structural assignment. Based on the evaluation of 1H–13C long-range coupling constants a rule of thumb could be deduced for an easy and unambiguous differentiation between the possible regioisomers formed. DFT frontier orbital calculations of the reactants offer an interesting tool to explain the regioselectivity of the key reaction.

Graphical abstract: Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation

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Publication details

The article was received on 04 Jan 2011, accepted on 01 Feb 2011 and first published on 02 Feb 2011


Article type: Paper
DOI: 10.1039/C1OB00012H
Citation: Org. Biomol. Chem., 2011,9, 2667-2673
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    Laccase-catalyzed phenol oxidation. Rapid assignment of ring-proton deficient polycyclic benzofuran regioisomers by experimental 1H–13C long-range coupling constants and DFT-predicted product formation

    H. Leutbecher, G. Greiner, R. Amann, A. Stolz, U. Beifuss and J. Conrad, Org. Biomol. Chem., 2011, 9, 2667
    DOI: 10.1039/C1OB00012H

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