Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones

doi:https://doi.org/10.1016/j.cherd.2014.08.021

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:

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

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

Publication Date:: 2014-09-03

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.

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                    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

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                    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.

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@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}

}

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Cited by: 7 works

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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
https://doi.org/10.1007/s00253-016-7987-5

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
https://doi.org/10.3390/catal8060223

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

Abstract

Citation Formats

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Dioxygen Activation by Laccases: Green Chemistry for Fine Chemical Synthesis journal, May 2018

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