Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 41, Pages 13389-13397Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b08756
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Funding
- European Research Council [ERC-2011-StG-277801]
- Spanish MINECO [CTQ2013-43012-P, CSD2010-00065, INP-2011-0059-PCT-420000-ACT1]
- Generalitat de Catalunya [2014 SGR 862]
- Universitat de Girona
- Spanish MINECO
- ICREA-Academia
- UdG
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Au has been demonstrated to mediate a number of organic transformations through the utilization of its pi 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-sp2-O bond formation reactions utilizing a model aryl halide macrocyclic substrate. Additionally, the halide exchange and C-sp2-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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