Issue 35, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2018,9, 7133-7137

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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