☆ 4.8 Article

Unprecedented Directing Group Ability of Cyclophanes in Arene Fluorinations with Diaryliodonium Salts

ORGANIC LETTERS (2011)

期刊

ORGANIC LETTERS

卷 13, 期 12, 页码 3158-3161

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol201080c

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Chemistry, Organic

资金

National Science Foundation [CHE 0717562]

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摘要

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.

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