Issue 5, 2007
From the journal:

Green Chemistry

One-pot synthesis of 1,4-naphthoquinones and related structures with laccase

Suteera Witayakrana  and  Arthur J. Ragauskas*a  

* Corresponding authors

a School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA, USA
E-mail: arthur.ragauskas@chemistry.gatech.edu
Fax: +1 404 894 4778
Tel: +1 404 894 9701

Abstract

The one-pot synthesis of 1,4-naphthoquinones by the Diels–Alder reaction of dienes with para-quinones generated in situ with laccase (EC 1.10.3.2, p-diphenol:dioxygen oxidoreductase) in an aqueous medium was developed in this study. The para-quinones were generated in situ by the laccase oxidation of the corresponding 1,4-hydroquinones and subsequently underwent the Diels–Alder reaction with dienes, and further oxidation to finally generate 1,4-naphthoquinones, in good yields. This reaction methodology provides unique green chemistry synthesis for isolation of the naphthoquinones, and without relying on organic solvents or hazardous heavy metal reagents. In this paper, the effects of laccase dose, temperature, and substrate sensitivity on the overall reaction were investigated.

Graphical abstract: One-pot synthesis of 1,4-naphthoquinones and related structures with laccase

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Article information

DOI
https://doi.org/10.1039/B606686K
Article type
Paper
Submitted
15 Jun 2006
Accepted
18 Jan 2007
First published
05 Feb 2007

Green Chem., 2007,9, 475-480

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One-pot synthesis of 1,4-naphthoquinones and related structures with laccase

S. Witayakran and A. J. Ragauskas, Green Chem., 2007, 9, 475 DOI: 10.1039/B606686K

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