title: Palladium-catalyzed C-H activation of N-allyl imines: regioselective allylic alkylations to deliver substituted aza-1,3-dienes.
abstract: A new mode of activation of an imine via a rare aza-substituted π-allyl complex is described. Palladium-catalyzed C(sp(3))-H activation of the N-allyl imine and the subsequent nucleophilic attack by the α-alkyl cyanoester produced the 1-aza-1,3-diene as the sole regioisomer. In contrast, nucleophilic attack by the α-aryl cyanoester exclusively delivered the 2-aza-1,3-diene, which was employed in an inverse-electron-demand Diels-Alder reaction for heterobiaryl synthesis.
authors: Department of Chemistry, Stanford University, Stanford, California 94305-5580 (USA). bmtrost@stanford.edu.
authors: Barry M
authors: BM
authors: Trost
authors: Subham
authors: S
authors: Mahapatra
authors: Martin
authors: M
authors: Hansen
keywords: CH activation; allylic compounds; heterocycles; palladium; synthetic methods