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Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides.

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.

SUBMITTER: Dorn SC

PROVIDER: S-EPMC4446700 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Nickel-catalyzed reductive arylation of activated alkynes with aryl iodides.

Dorn Stephanie C M SC Olsen Andrew K AK Kelemen Rachel E RE Shrestha Ruja R Weix Daniel J DJ

Tetrahedron letters 20150601 23

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 y ...[more]

PMID: 26028781

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