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:
-
- 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. https://doi.org/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. https://doi.org/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},
url = {https://www.osti.gov/biblio/1376566},
journal = {Chemical Engineering Research and Design},
issn = {0263-8762},
number = ,
volume = 97,
place = {United States},
year = {2014},
month = {9}
}
Web of Science
Works referencing / citing this record:
Laccase catalysis for the synthesis of bioactive compounds
journal, November 2016
- Kudanga, Tukayi; Nemadziva, Blessing; Le Roes-Hill, Marilize
- Applied Microbiology and Biotechnology, Vol. 101, Issue 1
Dioxygen Activation by Laccases: Green Chemistry for Fine Chemical Synthesis
journal, May 2018
- Romero-Guido, Cynthia; Baez, Antonino; Torres, Eduardo
- Catalysts, Vol. 8, Issue 6