Laccase-catalyzed α-arylation of benzoylacetonitrile with substituted hydroquinones

被引：9

作者：

Cannatelli, Mark D. ^{[1
]}

Ragauskas, Arthur J. ^{[1
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, Inst Paper Sci & Technol, Atlanta, GA 30332 USA

来源：

CHEMICAL ENGINEERING RESEARCH & DESIGN | 2015年 / 97卷

关键词：

alpha-Arylation; Benzylic nitrile; Green chemistry; Hydroquinones; Laccase; Benzoylacetonitrile; DOMINO REACTIONS; ANTIMICROBIAL ACTIVITY; ARYL HALIDES; NITRILES; DERIVATIVES; CYANOMETHYLATION; ALKYLATION; CHEMISTRY; OXIDATION; CATECHOLS;

D O I：

10.1016/j.cherd.2014.08.021

中图分类号：

TQ [化学工业];

学科分类号：

0817 ;

摘要：

The current study investigated a green method for alpha-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 H2O as their only by-product, to perform this transformation is an environmentally benign method for alpha-arylation of primary nitriles. (C) 2014 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved.

引用

页码：128 / 134

页数：7

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