What is it about?
Candida antarctica lipase B (CAL B) usually catalyzes esterifications or hydrolyses in the cells. Here, acts as an aminolysis catalyst for methyl esters and propargyl amine, an alkyne. Without isolation or separation palladium and copper catalysts are added to cross-couple amidated alkynes with (hetero)aryl iodides to give 3-(hetero)aryl substituted propargyl amides in good yield.
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Why is it important?
The combination of enzymes and metal catalysts in a single reaction vessel is unique and allows accessing more complex structures from simple starting materials under mild reaction conditions by assembling three structural units in a one-pot fashion. The products can be employed in syntheses of heterocycles or functional materials.
Perspectives
The mild amidation (aminolysis) is excellently compatible with many functionalities, eventually also molecules for electronic or bioorganic applications are rapidly and selectively accessible by combination of enzyme and metal catalysis.
Professor Thomas J J Müller
Heinrich-Heine-Universitat Dusseldorf
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This page is a summary of: Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis–Sonogashira coupling sequence, Organic & Biomolecular Chemistry, January 2015, Royal Society of Chemistry,
DOI: 10.1039/c4ob02386b.
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