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Title: Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones

Abstract

This article investigates a green method for α-arylation of a primary nitrile. Compounds possessing a benzylic nitrile have shown to exhibit biological activity. Laccases (benzenediol:oxygen oxidoreductase EC 1.10.3.2) were used as the catalysts to perform the cross-coupling reaction between benzoylacetonitrile and substituted hydroquinones. The corresponding 2-substituted 3-oxo-3-phenylpropanenitriles where synthesized in moderate to excellent yields in pH 7.0 buffered water under mild conditions. The substituent on the hydroquinone had a significant impact on product yields and regioselectivity of reaction. The use of laccases, which require O 2 as their only co-substrate and produce H 2O as their only by-product, to perform this transformation is an environmentally benign method for α-arylation of primary nitriles.

Authors:
 [1];  [1]
  1. Georgia Inst. of Technology, Atlanta, GA (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1376566
Grant/Contract Number:
AC05-00OR22725
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Chemical Engineering Research and Design
Additional Journal Information:
Journal Volume: 97; Journal ID: ISSN 0263-8762
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Cannatelli, Mark D., and Ragauskas, Arthur J.. Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones. United States: N. p., 2014. Web. doi:10.1016/j.cherd.2014.08.021.
Cannatelli, Mark D., & Ragauskas, Arthur J.. Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones. United States. doi:10.1016/j.cherd.2014.08.021.
Cannatelli, Mark D., and Ragauskas, Arthur J.. Wed . "Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones". United States. doi:10.1016/j.cherd.2014.08.021. https://www.osti.gov/servlets/purl/1376566.
@article{osti_1376566,
title = {Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones},
author = {Cannatelli, Mark D. and Ragauskas, Arthur J.},
abstractNote = {This article investigates a green method for α-arylation of a primary nitrile. Compounds possessing a benzylic nitrile have shown to exhibit biological activity. Laccases (benzenediol:oxygen oxidoreductase EC 1.10.3.2) were used as the catalysts to perform the cross-coupling reaction between benzoylacetonitrile and substituted hydroquinones. The corresponding 2-substituted 3-oxo-3-phenylpropanenitriles where synthesized in moderate to excellent yields in pH 7.0 buffered water under mild conditions. The substituent on the hydroquinone had a significant impact on product yields and regioselectivity of reaction. The use of laccases, which require O2 as their only co-substrate and produce H2O as their only by-product, to perform this transformation is an environmentally benign method for α-arylation of primary nitriles.},
doi = {10.1016/j.cherd.2014.08.021},
journal = {Chemical Engineering Research and Design},
number = ,
volume = 97,
place = {United States},
year = {Wed Sep 03 00:00:00 EDT 2014},
month = {Wed Sep 03 00:00:00 EDT 2014}
}

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