Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon–Nitrogen Bond Formation
Calvin Q. O’Broin, Patrick J. Guiry
Abstract
A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
Topics & Concepts
ChemistryPropargylPalladiumCatalysisNitrogenCarbon fibersOrganic chemistryCarbon–carbon bondMedicinal chemistryMaterials scienceComposite numberComposite materialCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsAsymmetric Hydrogenation and Catalysis