Anhydride-Additive-Free Nickel-Catalyzed Deoxygenation of Carboxylic Acids to Olefins

Abstract

A nickel-catalyzed route for direct, anhydride-additive-free deoxygenation of fatty acids to the corresponding olefins has been developed. The transformation is catalyzed by simple nickel salts of the type NiX<sub>2</sub> (X = halide, acetate, acetylacetonate), uses PPh<sub>3</sub> as a stoichiometric reductant, and exhibits selectivity for generation of linear α-olefin products. The reaction was rendered cocatalytic in PPh<sub>3</sub> using 1,1,3,3-tetramethyldisiloxane (TMDS) as terminal reductant for the in situ reduction of OPPh<sub>3</sub> and catalytic Cu­(OTf)<sub>2</sub>

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