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Issue 35, 2018
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meta-C–H arylation of fluoroarenes via traceless directing group relay strategy

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Abstract

While several methods for the ortho selective arylation of fluoroarenes, meta-functionalisation has never been achieved. We report a new methodology, based on the traceless directing group relay concept, leading to the first meta-selective (hetero)arylation of fluoroarenes. In this strategy, CO2 is introduced as a transient directing group, to control a Pd-catalysed arylation meta to the fluoro functionality, prior to its release in a sequential, one-pot fashion. This method has shown compatibility with a number of functional groups and substitution patterns in both the fluoroarene core and aryl iodide coupling partners, and proceeds with complete meta-selectivity and mono vs. bis-arylation selectivity.

Graphical abstract: meta-C–H arylation of fluoroarenes via traceless directing group relay strategy

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Publication details

The article was received on 01 Jun 2018, accepted on 25 Jul 2018 and first published on 25 Jul 2018


Article type: Edge Article
DOI: 10.1039/C8SC02417K
Chem. Sci., 2018,9, 7133-7137
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    meta-C–H arylation of fluoroarenes via traceless directing group relay strategy

    M. Font, A. R. A. Spencer and I. Larrosa, Chem. Sci., 2018, 9, 7133
    DOI: 10.1039/C8SC02417K

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