Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 48, Pages 19386-19392Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2058567
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Funding
- MICINN of Spain [CTQ2009-08464/BQU, CTQ2008-03077/BQU, CTQ2011-23156/BQU, Consolider-Ingenio CSD2010-00065]
- European Research Council [ERC-2011-StG-277801]
- Catalan DIUE of the Generalitat de Catalunya [2009SGR637]
- ICREA
- Centre de Serveis Cientifics i Academics de Catalunya (CESCA)
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Copper-catalyzed halide exchange reactions under very mild reaction conditions are described for the first time using a family of model aryl halide substrates. All combinations of halide exchange (I, Br, Cl, F) are observed using catalytic amounts of Cu-I. Strikingly, quantitative fluorination of aryl X substrates is also achieved catalytically at room temperature, using common F- sources, via the intermediacy of aryl-Cu-III-X species. Experimental and computational data support a redox Cu-I/Cu-III catalytic cycle involving aryl X oxidative addition at the Cu-I center, followed by halide exchange and reductive elimination steps. Additionally, defluorination of the aryl-F model system can be also achieved with Cu-I at room temperature operating under a Cu-I/Cu-III redox pair.
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