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Oxidant-Free Au(I)-Catalyzed Halide Exchange and C(sp2)-O Bond Forming Reactions

Oxidant-Free Au(I)-Catalyzed Halide Exchange and C(sp2)-O Bond Forming Reactions

Journal of the American Chemical Society 137(41): 13389-13397

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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Accession: 058488158

Download citation: RISBibTeXText

PMID: 26397959

DOI: 10.1021/jacs.5b08756

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