Journal of Oleo Science 2007-01-01

Synthesis of novel trifluoromethyl-bearing bifunctional acyl-acceptant arenes: 2,2'-bis(trifluoromethylated aryloxy)biphenyls.

Akiko Okamoto, Katsuya Maeyama, Keiichi Noguchi, Hideaki Oike, Yoshihiko Murakami, Noriyuki Yonezawa

Index: J. Oleo Sci. 56(9) , 479-91, (2007)

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Abstract

Novel bifunctional acyl-acceptant biphenyls bearing trifluoromethylated aroyloxy groups were successfully synthesized in high yields via TfOH-mediated electrophilic aromatic aroylation of fluorobenzene with CF(3)-bearing aroyl chlorides followed by nucleophilic aromatic substitution with 2,2'-biphenol. Similarly, 2,2'-bis(trifluoromethylphenoxy)biphenyl was synthesized via nucleophilic aromatic substitution of 4-fluorobenzotrifluoride with 2,2'-biphenol. These 2,2'-bis(trifluoromethylated aryloxy)biphenyls show good regioselectivity and successive reactivity in electrophilic aromatic aroylation with p-toluic acid/p-toluoyl chloride according to the structure of the substrate biphenyls, implying their sufficient potential as acyl-accepting precursor molecules for synthesis of aromatic compounds bearing characteristic interfacial properties attributed to CF(3) groups.