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Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts.

ABSTRACT: For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.

SUBMITTER: Graskemper JW

PROVIDER: S-EPMC3126865 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts.

Graskemper Joseph W JW Wang Bijia B Qin Linlin L Neumann Kiel D KD DiMagno Stephen G SG

Organic letters 20110517 12

For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium ...[more]

PMID: 21591627

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