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Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

ABSTRACT: Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C-C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ?-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates.

SUBMITTER: Pitts CR

PROVIDER: S-EPMC5669245 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

Pitts Cody Ross CR Bloom Michelle Sheanne MS Bume Desta Doro DD Zhang Qinze Arthur QA Lectka Thomas T

Chemical science 20150623 9

Expanding the repertoire of controlled radical fluorination techniques, we present a photosensitized unstrained C-C bond activation/directed monofluorination method using Selectfluor and 9-fluorenone. The reaction is amenable to the opening of multiple 1-acetal-2-aryl substituted rings to yield ω-fluoro carboxylic acids, esters, alcohols, and ketones with relative ease. Initial mechanistic insight suggests radical ion intermediates. ...[more]

PMID: 29449927

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