Aerobic Zinc-Catalyzed Synthesis of β-Nitroalkenes through the Nitration of Alkenes with Potassium Nitrite

Abstract

Zinc-catalyzed reaction of terminal aryl alkenes with potassium nitrite selectively affords (E)-β-nitroalkenes under air atmosphere. The transformation is promoted by the reaction of potassium nitrite with acetic anhydride in air and proceeds through a zinc-catalyzed radical process. Terminal aryl alkenes provide the desired products in good yields, whereas alkyl alkenes and internal alkenes exhibit substantially lower reactivity.