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Reductive hydrobenzylation of terminal alkynes via photoredox and nickel dual catalysis.

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A photoredox/nickel dual catalyzed reductive hydrobenzylation of alkynes and benzyl chlorides by employing alkyl amines as a stoichiometric reductant is described. This synergistic protocol proceeds via Markovnikov-selective migratory insertion of… Click to show full abstract

A photoredox/nickel dual catalyzed reductive hydrobenzylation of alkynes and benzyl chlorides by employing alkyl amines as a stoichiometric reductant is described. This synergistic protocol proceeds via Markovnikov-selective migratory insertion of an alkyne into nickel hydride, followed by cross-coupling with benzyl chloride, providing facile access to important 1,1-disubstituted olefins. This reaction enables the generation of nickel hydride by utilizing readily available alkyl amines as the hydrogen source. The mild conditions are compatible with a wide range of aryl and alkyl alkynes as well as chlorides.

Keywords: photoredox nickel; hydrobenzylation terminal; reductive hydrobenzylation; nickel dual

Journal Title: Chemical communications
Year Published: 2021

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