Palladium-Catalyzed Oxidative Amination of Unactivated Olefins with Primary Aliphatic Amines.
J Am Chem Soc
; 145(17): 9448-9453, 2023 May 03.
Article
em En
| MEDLINE
| ID: mdl-37053042
ABSTRACT
Direct coupling of unactivated olefins with primary alkylamines is considered to be an efficient but unknown method for the construction of complex amines. Herein we report a catalytic intermolecular oxidative amination of unactivated olefins with primary aliphatic amines based on the combination of a palladium catalyst, a bidentate phosphine ligand, and duroquinone. A range of secondary allylic amines were obtained in good yields with excellent regio- and stereoselectivity. Mechanistic control experiments revealed that the reaction proceeds by allylic C(sp3)-H activation and nucleophilic amination. The utility of the protocol is further demonstrated with the late-stage modification and streamlined synthesis of drug molecules.
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MEDLINE
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En
Ano de publicação:
2023
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Article