Synthesis of novel trifluoromethyl-bearing bifunctional acyl-acceptant arenes: 2,2'-bis(trifluoromethylated aryloxy)biphenyls.
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.
Okamoto
Akiko
A
Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo, Japan.
Maeyama
Katsuya
K
Noguchi
Keiichi
K
Oike
Hideaki
H
Murakami
Yoshihiko
Y
Yonezawa
Noriyuki
N
D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001713:Biphenyl Compounds; D005659:Fungicides, Industrial; D006841:Hydrocarbons, Aromatic; D006845:Hydrocarbons, Fluorinated