Synthesis of Novel Trifluoromethyl-bearing Bifunctional Acyl-acceptant Arenes: 2,2’-Bis(trifluoromethylated aryloxy)biphenyls

• Published in: Journal of Oleo Science Vol. 56; no. 9; pp. 479 - 491
• Main Authors: Okamoto, Akiko, Maeyama, Katsuya, Noguchi, Keiichi, Oike, Hideaki, Murakami, Yoshihiko, Yonezawa, Noriyuki
• Format: Journal Article
• Language: English
• Published: Japan Oil Chemists' Society 2007
• Subjects: bifunctional acyl-acceptant biphenyls; CF3-bearing aromatic ring assembly; electrophilic aromatic aroylation; nucleophilic aromatic substitution
• ISSN: 1345-8957; 1347-3352
• DOI: 10.5650/jos.56.479

Novel bifunctional acyl-acceptant biphenyls bearing trifluoromethylated aroyloxy groups were successfully synthesized in high yields via TfOH-mediated electrophilic aromatic aroylation of fluorobenzene with CF3-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 CF3 groups.