Oxidant-Free
Au(I)-Catalyzed Halide Exchange and C<sub>sp2</sub>–O Bond
Forming Reactions
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Abstract
Au
has been demonstrated to mediate a number of organic transformations
through the utilization of its π Lewis acid character, Au(I)/Au(III)
redox properties or a combination of both. As a result of the high
oxidation potential of the Au(I)/Au(III) couple, redox catalysis involving
Au typically requires the use of a strong external oxidant. This study
demonstrates unusual external oxidant-free Au(I)-catalyzed halide
exchange (including fluorination) and C<sub>sp2</sub>–O bond
formation reactions utilizing a model aryl halide macrocyclic substrate.
Additionally, the halide exchange and C<sub>sp2</sub>–O coupling
reactivity could also be extrapolated to substrates bearing a single
chelating group, providing further insight into the reaction mechanism.
This work provides the first examples of external oxidant-free Au(I)-catalyzed
carbon–heteroatom cross-coupling reactions