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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.

SUBMITTER: Font M

PROVIDER: S-EPMC6137440 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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

Font Marc M Spencer Andrew R A ARA Larrosa Igor I

Chemical science 20180725 35

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 fa ...[more]

PMID: 30310635

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