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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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Supplementary files

Article information


Submitted
01 Jun 2018
Accepted
25 Jul 2018
First published
25 Jul 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 7133-7137
Article type
Edge Article

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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