Palladium‐Mediated C<sub>γ</sub>−H Functionalization of Alicyclic Amines
Ellen Y. Aguilera, Melanie S. Sanford
Abstract
Abstract This paper describes a new method for the transannular functionalization of the γ‐C−H bonds in alicyclic amines to install C(sp 3 )−halogen, oxygen, nitrogen, boron, and sulfur bonds. The key challenge for this transformation is controlling the relative rate of C γ −H versus C α −H functionalization. We demonstrate that this selectivity can be achieved by pre‐complexation of the substrate with Pd prior to the addition of oxidant. This approach enables the use of diverse oxidants that ultimately install various heteroatom functional groups at the γ‐position with high site‐ and diastereoselectivity.
Topics & Concepts
Alicyclic compoundSurface modificationChemistryHeteroatomPalladiumSulfurSubstrate (aquarium)BoronSelectivityCombinatorial chemistryOrganic chemistryRing (chemistry)CatalysisPhysical chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions