Nickel Dual Photoredox Catalysis for the Synthesis
of Aryl Amines
Ryan J. Key
Aaron K. Vannucci
10.1021/acs.organomet.8b00121.s001
https://acs.figshare.com/articles/journal_contribution/Nickel_Dual_Photoredox_Catalysis_for_the_Synthesis_of_Aryl_Amines/6163742
In 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.
2018-04-19 20:29:31
ambient conditions
catalyst loadings
photoredox-assisted reductive
aryl amines
nickel photocatalysis
aryl halides
N-radical mechanism
electron donor
Photoredox Catalysis
Ru photocatalyst
nickel cross-coupling catalyst
nickel catalyst
amination mechanism proceeds
photoredox nickel catalysis system
redox-neutral cross-coupling system
Aryl Amines
triaryl amines
bond