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.
Highlights
Fluoroarenes are recurring structural motifs in pharmaceuticals, agrochemicals, biological imaging agents and organic materials.[1]
We turned our attention to optimising the tandem arylation/protodecarboxylation process in order to obtain the desired meta-arylated uoroarene products in a one-pot process
Examination of reaction conditions previously developed for the tandem arylation/decarboxylation of benzoic acids14c gave mixtures of the desired meta-arylation product 3aa and the corresponding non-decarboxylated arylation product 4aa even at high temperatures
Summary
Fluoroarenes are recurring structural motifs in pharmaceuticals, agrochemicals, biological imaging agents and organic materials.[1]. While several methods for the ortho selective arylation of fluoroarenes, meta-functionalisation has never been achieved. 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.
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