Photoinduced Desaturation of Amides by Palladium Catalysis.

Abstract

A photoinduced palladium-catalyzed desaturation method that is suitable for converting the linear amides to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium and oxidant reagents and can be carried out at room temperature through a simple one-step operation. The protocol exhibits great scalability and functional group tolerance. The reaction mechanism has been investigated through deuterium labeling experiments, radical clock, radical capture, and kinetic studies. Mechanistic studies suggested a radical pathway involving aryl/alkyl Pd-radical intermediates.