Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Abstract

Herein we report an iron-catalyzed, convenient and expedient strategy for the synthesis of styrene and naphthalene deriva-tives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- and N-heterocyclic compounds) and can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation / double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate determining step.