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Brønsted Acid Mediated (sp 3 )Carbon‐Fluorine Bond Activation: Inter‐ and Intramolecular Arylation of Trifluoromethylated Arenes
Author(s) -
WANG Fei,
HU Jinbo
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990032
Subject(s) - triflic acid , chemistry , intramolecular force , nucleophile , brønsted–lowry acid–base theory , trifluoromethylation , catalysis , hydrogen bond , medicinal chemistry , benzene , aryl , fluorine , acid catalysis , organic chemistry , trifluoromethyl , molecule , alkyl
Trifluoromethanesulfonic acid (triflic acid) was found to be able to efficiently activate the benzylic sp 3 C–F bond. Thus, under the catalysis of triflic acid at room temperature, trifluoromethylated arenes readily reacted with benzene to give benzophenones in moderate to good yields. Under similar B?nsted acid catalysis, intramolecular arylation also happened in the cases of some CF 3 ‐arene substrates bearing an additional nucleophilic aryl group. Strong CF···H + interaction or hydrogen bonding, is believed to play an important role in the current Br?nsted acid‐mediated C–F bond activation chemistry.