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Molecules 2018, 23(9), 2227; https://doi.org/10.3390/molecules23092227

Heck Transformations of Biological Compounds Catalyzed by Phosphine-Free Palladium

Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland
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Received: 30 June 2018 / Revised: 29 August 2018 / Accepted: 29 August 2018 / Published: 1 September 2018
(This article belongs to the Special Issue Chemical Transformation of Renewable Material for Green Chemistry)
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Abstract

The development and optimization of synthetic methods leading to functionalized biologically active compounds is described. Two alternative pathways based on Heck-type reactions, employing iodobenzene or phenylboronic acid, were elaborated for the arylation of eugenol and estragole. Cinnamyl alcohol was efficiently transformed to saturated arylated aldehydes in reaction with iodobenzene using the tandem arylation/isomerization sequential process. The arylation of cinnamyl alcohol with phenylboronic acid mainly gave unsaturated alcohol, while the yield of saturated aldehyde was much lower. Catalytic reactions were carried out using simple, phosphine-free palladium precursors and water as a cosolvent, following green chemistry rules as much as possible. View Full-Text
Keywords: palladium; arylation; Heck coupling; cinnamyl alcohol; linalool; eugenol; estragole palladium; arylation; Heck coupling; cinnamyl alcohol; linalool; eugenol; estragole
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Tarnowicz-Ligus, S.; Trzeciak, A.M. Heck Transformations of Biological Compounds Catalyzed by Phosphine-Free Palladium. Molecules 2018, 23, 2227.

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