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

SERRA, Jordi, WHITEOAK, Christopher, ACUÑA-PARÉS, Ferran, FONT, Marc, LUIS, Josep M., LLORET-FILLOL, Julio and RIBAS, Xavi (2015). Oxidant-Free Au(I)-Catalyzed Halide Exchange and Csp2–O Bond Forming Reactions. Journal of the American Chemical Society, 137 (41), 13389-13397.

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Official URL: http://dx.doi.org/10.1021/jacs.5b08756
Link to published version:: 10.1021/jacs.5b08756


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.

Item Type: Article
Identification Number: 10.1021/jacs.5b08756
Depositing User: Christopher Whiteoak
Date Deposited: 04 Apr 2016 13:25
Last Modified: 23 Oct 2016 21:44
URI: http://shura.shu.ac.uk/id/eprint/11769

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