Abstract
An efficient procedure for the direct arylation of pyrrolidine with phenols and naphtols is reported. Upon reaction with catalytic amounts of a binuclear copper(II)-7-azaindole complex under an atmosphere of oxygen, pyrrolidine is smoothly oxidized to the corresponding imine which can be trapped in situ by a series of phenols and naphtols in fair to good yields. This copper-catalyzed direct oxidative arylation of pyrrolidine offers an efficient entry to α-aryl-pyrrolidines in a single step and without the need for protecting or directing groups.
Keywords: Amine oxidation, C-H functionalization, copper catalysis, direct arylation, imines, pyrrolidines.
Graphical Abstract
Letters in Organic Chemistry
Title:Copper-Catalyzed Direct Oxidative α-Arylation of Pyrrolidine with Phenols and Naphtols
Volume: 15 Issue: 5
Author(s): Phideline Gerard and Gwilherm Evano*
Affiliation:
- Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Universite libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels,Belgium
Keywords: Amine oxidation, C-H functionalization, copper catalysis, direct arylation, imines, pyrrolidines.
Abstract: An efficient procedure for the direct arylation of pyrrolidine with phenols and naphtols is reported. Upon reaction with catalytic amounts of a binuclear copper(II)-7-azaindole complex under an atmosphere of oxygen, pyrrolidine is smoothly oxidized to the corresponding imine which can be trapped in situ by a series of phenols and naphtols in fair to good yields. This copper-catalyzed direct oxidative arylation of pyrrolidine offers an efficient entry to α-aryl-pyrrolidines in a single step and without the need for protecting or directing groups.
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Cite this article as:
Gerard Phideline and Evano Gwilherm *, Copper-Catalyzed Direct Oxidative α-Arylation of Pyrrolidine with Phenols and Naphtols, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178614666171120164418
DOI https://dx.doi.org/10.2174/1570178614666171120164418 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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