Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides

Dorn, S., A. Olsen, R. Kelemen, R. Shrestha, and D. Weix. Nickel-Catalyzed Reductive Arylation of Activated Alkynes With Aryl Iodides. Tetrahedron Lett., 3367.
Abstract The direct, regioselective, and stereoselective arylation of activated alkynes with aryl iodides using a nickel catalyst and manganese reductant is described. The reaction conditions are mild (40 °C in MeOH, no acid or base) and an intermediate organomanganese reagent is unlikely. Functional groups tolerated include halides and pseudohalides, free and protected anilines, and a benzyl alcohol. Other activated alkynes including an amide and a ketone also reacted to form arylated products in good yields.
Keywords alkynealpha,beta-acetylenic estersarylationcatalyzedconjugate additioncyclizationderivativesefficienthydroarylationmild conditionsnickelorganic halidesorganoboronic acidsreagentsreductive
DOI 10.1016/j.tetlet.2015.02.120