01329nas a2200205 4500008004100000022001400041245006100055210005900116260000900175300001400184490000700198520069300205100002200898700001700920700001800937700002600955700002500981700002501006856009201031 2020 eng d a0022-326300aIron-catalyzed direct julia-type olefination of alcohols0 aIroncatalyzed direct juliatype olefination of alcohols cAUG a9876-98860 v853 a
Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives 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) that 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.
1 aLandge, Vinod, G.1 aBabu, Reshma1 aYadav, Vinita1 aSubaramanian, Murugan1 aGupta, Virendrakumar1 aBalaraman, Ekambaram uhttp://library.ncl.res.in/content/iron-catalyzed-direct-julia-type-olefination-alcohols