Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide

A practical and direct method for the alpha,beta-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.