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C–N Bond Coupling of Fluorobenzenes: N‐Heterocycle‐Assisted Selective C–F Bond Cleavage through an Li/F Interaction
Author(s) -
Chen Jianping,
Huang Dongyang,
Ding Yuqiang
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700623
Subject(s) - chemistry , amination , bond cleavage , ring (chemistry) , pyridine , cleavage (geology) , benzene , coupling (piping) , coupling reaction , catalysis , medicinal chemistry , stereochemistry , photochemistry , organic chemistry , mechanical engineering , geotechnical engineering , fracture (geology) , engineering
We describe a method for the cross‐coupling of fluoroarenes with amines. The reaction involves an N‐heterocycle‐assisted selective C–F bond cleavage, and does not require a transition‐metal catalyst. The cross‐coupling reaction is significantly promoted by an Li/F interaction. Unexpectedly, amination of an ortho C–F bond on the pyridine ring was observed for 2‐(2‐fluorophenyl)‐6‐fluoropyridine, while the C–F bond on the benzene ring remained intact.