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meta-C-H arylation of fluoroarenes via traceless directing group relay strategy
Marc Font1, Andrew R A Spencer1, Igor Larrosa1
1School of Chemistry , University of Manchester , Oxford Road , Manchester , M13 9PL , UK .
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.
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