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DESign of Sustainable One-Pot Chemoenzymatic Organic Transformations in Deep Eutectic Solvents for the Synthesis of 1,2-Disubstituted Aromatic Olefins

Nicolás Ríos‐Lombardía, María J. Rodríguez‐Álvarez, Francisco Morís, Robert Kourist, Natalia Comino, Fernando López‐Gallego, Javier González‐Sabín, Joaquín García‐Álvarez

2020Frontiers in Chemistry29 citationsDOIOpen Access PDF

Abstract

The self-assembly of styrene-type olefins into the corresponding stilbenes was conveniently performed in the Deep Eutectic Solvent (DES) mixture 1ChCl/2Gly under air and in the absence of hazardous organic co-solvents using a one-pot chemo-biocatalytic route. Here, an enzymatic decarboxylation of p-hydroxycinnamic acids sequentially followed by a ruthenium-catalyzed metathesis of olefins has been investigated in DES solvent. Moreover, and to extend the design of chemoenzymatic processes in DESs, we also coupled the aforementioned enzymatic decarboxylation reaction to now concomitant Pd-catalyzed Heck-type C-C coupling to produce biaryl derivatives under environmentally friendly reaction conditions.

Topics & Concepts

DecarboxylationChemistryOrganic chemistryCatalysisDeep eutectic solventEutectic systemSolventEnvironmentally friendlyGreen chemistryStyreneMetathesisReaction mechanismPolymerizationCopolymerPolymerAlloyEcologyBiologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions