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

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, CO 2...

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Bibliographic Details
Published in:Chemical science (Cambridge) Vol. 9; no. 35; pp. 7133 - 7137
Main Authors: Font, Marc, Spencer, Andrew R. A., Larrosa, Igor
Format: Journal Article
Language:English
Published: CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects:
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Functional groups
Physical Sciences
Science & Technology
Selectivity
PALLADIUM
ACTIVATION
SELECTIVE ARYLATION
ARYL
LIGAND
FLUORINE CHEMISTRY
ORTHO-METALATION
SIMPLE ARENES
CARBOXYLIC-ACIDS
BENZOIC-ACIDS
ISSN:2041-6520, 2041-6539
Online Access:Get full text
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Summary: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, CO 2 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.
Bibliography:UKRI
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ISSN:2041-6520
2041-6539
DOI:10.1039/C8SC02417K