Oxidant-Free Au(I)-Catalyzed Halide Exchange and Csp2–O Bond Forming Reactions

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Serra, Jordi ; Whiteoak, Christopher ; Acuña-Parés, Ferran ; Font, Marc ; Luis, Josep M. ; Lloret-Fillol, Julio ; Ribas, Xavi (2015)

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 Csp2–O bond formation reactions utilizing a model aryl halide macrocyclic substrate. Additionally, the halide exchange and Csp2–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.
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