Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation

A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium­(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-h...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-05, Vol.138 (18), p.5805-5808
Main Authors: Gurak, John A, Yang, Kin S, Liu, Zhen, Engle, Keary M
Format: Article
Language:English
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Summary:A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium­(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized γ-amino acids in good yields with high regioselectivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b02718