Issue 31, 2020
From the journal:

New Journal of Chemistry

Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine complex under microwave irradiation†

Juan C. Jiménez-Cruz,a   Ramón Guzmán-Mejía, ORCID logo a   Eusebio Juaristi, ORCID logo *bc   Omar Sánchez-Antonio,b   Marco A. García-Revilla,*d   J. Betzabe González-Camposa  and  Judit Aviña-Verduzco ORCID logo *a  

* Corresponding authors

a Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Edificio B-1, planta baja Ciudad Universitaria, 58030 Morelia, Michoacán, Mexico
E-mail: jaavina@umich.mx

b Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida Instituto Politécnico, Nacional # 2508, 07360 Ciudad de México, Mexico

c El Colegio Nacional, Donceles No. 104, Centro Histórico, 06020 Ciudad de México, Mexico

d Departamento de Química, Universidad de Guanajuato, Noria Alta s/n, 36050 Guanajuato, Gto., Mexico

Abstract

A series of aromatic γ-hydroxyketones were prepared by means of Heck coupling reaction of aryl halides and 2,3-dihydrofuran, catalyzed by PdCl2·Gly2 and under microwave irradiation. This synthetic transformation involves the formation of an aryl-dihydrofuranoic intermediate, followed by an unusual opening of the heterocycle promoted by a water molecule and the formation of the ketone carbonyl function through keto–enol tautomerism.

Graphical abstract: Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine complex under microwave irradiation

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Article information

DOI
https://doi.org/10.1039/D0NJ02630A
Article type
Paper
Submitted
25 May 2020
Accepted
22 Jul 2020
First published
23 Jul 2020

New J. Chem., 2020,44, 13382-13392

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Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(II) glycine complex under microwave irradiation

J. C. Jiménez-Cruz, R. Guzmán-Mejía, E. Juaristi, O. Sánchez-Antonio, M. A. García-Revilla, J. B. González-Campos and J. Aviña-Verduzco, New J. Chem., 2020, 44, 13382 DOI: 10.1039/D0NJ02630A

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