Synthesis of Substituted 4‐Arylamino‐1,2‐naphthoquinones in One‐Pot Reactions Using CotA‐Laccase as Biocatalyst

An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4‐arylamino‐1,2‐naphthoquinones was developed, through a cross‐coupling reaction in which the 1,2‐naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA‐laccase from Bacillus subtilis,...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-08, Vol.362 (16), p.3380-3387
Main Authors: Sousa, Ana Catarina, Santos, Iolanda, Piedade, M. F. M. M., Martins, Lígia O., Robalo, M. Paula
Format: Article
Language:English
Subjects:
4-arylamino-1,2-naphthoquinones
Amines
biocatalysis
CotA-laccase
Cross coupling
green synthesis
Laccase
Substitutes
Sulfonic acid
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Summary:An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4‐arylamino‐1,2‐naphthoquinones was developed, through a cross‐coupling reaction in which the 1,2‐naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA‐laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochemical data and kinetic parameters were determined revealing a significant higher specificity of CotA‐laccase for 4‐amino‐3‐hydroxynaphthalene‐1‐sulfonic acid (AHNSA). This ability of CotA‐laccase to discriminate between oxidisable aromatic amines allows the set‐up of one‐pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000082