Synthesis of conjugated dienes via palladium-catalysed aerobic dehydrogenation of unsaturated acids and amides.

Abstract

A Pd(II)-catalyzed direct aerobic dehydrogenation of γ,δ-olefinic acids and amides has been demonstrated. The present protocol dehydrogenates the least acidic amides and acids, thus replacing the traditional enolate strategy for dehydrogenation. A broad spectrum of conjugated dienamides and dienoic acids were produced in good to excellent yields. A possible reaction mechanism was proposed and supported by deuterium labelling studies.