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Nickel Dual Photoredox Catalysis for the Synthesis of Aryl Amines
journal contribution
posted on 2018-04-19, 20:29 authored by Ryan J. Key, Aaron K. VannucciIn this work, a new dual photoredox
nickel catalysis system has
been utilized for the synthesize of aryl amines. Previously, our group
has shown that a nickel catalyst in conjunction with a photosensitizer
and a sacrificial electron donor can cross-couple C–C bonds
via photoredox-assisted reductive coupling. Here we have built upon
that system to develop a redox-neutral cross-coupling system for the
formation of C–N bonds. The catalytic system is composed of
just a nickel cross-coupling catalyst, a Ru photocatalyst, and base
and is capable of coupling amines with aryl halides in good to excellent
yields. Furthermore, it was found that these reactions are functional
under ambient conditions with catalyst loadings of 1 mol %. Spectroscopic
studies provide support that this amination mechanism proceeds via
a nitrogen-based radical intermediate. This N-radical mechanism offers
direct synthetic access to di- and triaryl amines from nickel photocatalysis.
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ambient conditionscatalyst loadingsphotoredox-assisted reductivearyl aminesnickel photocatalysisaryl halidesN-radical mechanismelectron donorPhotoredox CatalysisRu photocatalystnickel cross-coupling catalystnickel catalystamination mechanism proceedsphotoredox nickel catalysis systemredox-neutral cross-coupling systemAryl Aminestriaryl aminesbond
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