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

[ Vol. 15 , Issue. 5 ]

Author(s):

Phideline Gerard and Gwilherm Evano*   Pages 359 - 364 ( 6 )

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.

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, Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Universite libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels

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