title: Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides.
abstract: A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. yama@m.tohoku.ac.jp arisawa@m.tohoku.ac.jp.
authors.forename: Mieko
authors.initials: M
authors.lastname: Arisawa
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. yama@m.tohoku.ac.jp arisawa@m.tohoku.ac.jp.
authors.forename: Saori
authors.initials: S
authors.lastname: Tanii
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. yama@m.tohoku.ac.jp arisawa@m.tohoku.ac.jp.
authors.forename: Takeru
authors.initials: T
authors.lastname: Tazawa
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. yama@m.tohoku.ac.jp arisawa@m.tohoku.ac.jp.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Yamaguchi