Intermolecular 1,4-Carboamination of Conjugated Dienes Enabled by Cp*RhIII -Catalyzed C-H Activation.

ABSTRACT

A protocol for the three-component 1,4-carboamination of dienes is described. Synthetically versatile Weinreb amides were coupled with 1,3-dienes and readily available dioxazolones as the nitrogen source using [Cp*RhCl2 ]2 -catalyzed C-H activation to deliver the 1,4-carboaminated products. This transformation proceeds under mild reaction conditions and affords the products with high levels of regio- and E-selectivity. Mechanistic investigations suggest an intermediate RhIII -allyl species is trapped by an electrophilic amidation reagent in a redox-neutral fashion.