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A counteranion triggered arylation strategy using diaryliodonium fluorides.

ABSTRACT: A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic O-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstrating the compatibility of the arylation tactic with latent carbon nucleophiles.

SUBMITTER: Chan L

PROVIDER: S-EPMC5811167 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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A counteranion triggered arylation strategy using diaryliodonium fluorides.

Chan L L McNally A A Toh Q Y QY Mendoza A A Gaunt M J MJ

Chemical science 20141112 2

A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic <i>O</i>-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstra ...[more]

PMID: 29541441

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