Laccase cataylzed synthesis of quaternary malononitriles with an aryl substituent

Tetrahedron Green Chem Pub Date : 2025-06-01 Epub Date: 2025-01-26 DOI:10.1016/j.tgchem.2025.100066
Parisa Amani, Mansour Shahedi, Elaheh Rezaei, Zohreh Habibi
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Abstract

Synthesis of quaternary malononitriles with an aryl substituent is of great importance because these scaffolds serve as essential intermediates in the synthesis of bioactive compounds. This study presents an efficient method for the laccase-catalyzed arylation of 2-substituted malononitrile derivatives by oxidation of catechols using aerial oxygen as the oxidant, followed by the nucleophilic addition of 2-substituted malononitriles. The process achieves yields ranging from moderate to excellent (73–97 %), and also, it was associated with a slight decrease in efficiency in higher scales.

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漆酶催化合成含芳基取代基的季丙二腈
具有芳基取代基的季丙二腈的合成具有重要意义,因为这些支架是合成生物活性化合物必不可少的中间体。本研究提出了一种漆酶催化的2-取代丙二腈衍生物的芳基化方法,该方法采用空气氧作为氧化剂氧化儿茶酚,然后亲核加成2-取代丙二腈。该工艺的产率范围从中等到优异(73 - 97%),而且,在更高的规模下,它的效率会略有下降。
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