Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.cherd.2014.08.021

Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones

Journal Article · Wed Sep 03 00:00:00 EDT 2014 · Chemical Engineering Research and Design

DOI:https://doi.org/10.1016/j.cherd.2014.08.021· OSTI ID:1376566

Cannatelli, Mark D. ^[1]; Ragauskas, Arthur J. ^[1]

Georgia Inst. of Technology, Atlanta, GA (United States)

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.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1376566

Journal Information:: Chemical Engineering Research and Design, Journal Name: Chemical Engineering Research and Design Vol. 97; ISSN 0263-8762

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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