Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

Davy Baudelet; Adam Daïch; Benoît Rigo; Emmanuelle Lipka; Philippe Gautret; Germain Homerin; Christelle Claverie; Jolanta Rousseau; Cristina-Maria Abuhaie; Alina Ghinet

doi:10.1055/s-0035-1561415

Synthesis, Table of Contents

Synthesis 2016; 48(14): 2226-2244
DOI: 10.1055/s-0035-1561415

paper

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

Authors

Davy Baudelet

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France

^cUFR Pharmacie Lille, Laboratoire de Chimie Analytique, BP 83, 59006 Lille, France
Adam Daïch*

^dNormandie Univ, ULEHAVRE, CNRS, URCOM, 76600 Le Havre, France Email: adam.daich@univ-lehavre.fr
Benoît Rigo

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France
Emmanuelle Lipka

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^cUFR Pharmacie Lille, Laboratoire de Chimie Analytique, BP 83, 59006 Lille, France
Philippe Gautret

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France
Germain Homerin

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France
Christelle Claverie

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France
Jolanta Rousseau

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France
Cristina-Maria Abuhaie

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France

^eDepartment of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp-A, 700506 Iasi, Romania
Alina Ghinet*

^aInserm, U995-LIRIC, CHRU Lille, Faculté de Médecine-Pôle Recherche Université Lille 2, Place Verdun, 59045 Lille Cedex, France

^bLaboratoire de Pharmacochimie, Ecole des Hautes Etudes d’Ingénieur (HEI), 13 rue de Toul, 59046 Lille, France

^eDepartment of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp-A, 700506 Iasi, Romania

Abstract

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Abstract

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp²-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.

Key words

arylation - heterogeneous catalysis - copper - cross-coupling - lactams - heterocycles

Full Text

References

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