Michael John Rodriguez

A tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence: γ,δ-Unsaturated isoxazolines as precursors to ring-fused ethers

Abstract A tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence affords cis-fused octahydrobenzo-and hexahydro-2H-cyclopenta[b]furans via the intermediacy of γ,δ-unsaturated isoxazolines.

Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3

Boron-derived Lewis acids have been shown to effectively promote the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.