Copper-Catalyzed Direct Oxidative α-Arylation of Pyrrolidine with Phenols and Naphtols

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.

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