4.8 Article

Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 18, Pages 5805-5808

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b02718

Keywords

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Funding

  1. TSRI
  2. Pfizer, Inc.
  3. Donald E. and Delia B. Baxter Foundation
  4. National Science Foundation [NSF/DGE-1346837]

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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 beta-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized gamma-amino acids in good yields with high regioselectivity.

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