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Published on: November 9, 2019
Sigmatropic Dearomatization/Defluorination Strategy for C-F Transformation: Synthesis of Fluorinated Benzofurans from
Koichi Okamoto1, Mitsuki Hori1, Tomoyuki Yanagi1
1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
Abstract:
Facile synthesis of fluorinated benzofurans from polyfluorophenols has been accomplished by means of a sigmatropic dearomatization/defluorination strategy composed of three processes: (1) interrupted Pummerer reaction of ketene dithioacetal monoxides with polyfluorophenols followed by [3,3] sigmatropic rearrangement, (2) Zn-mediated smooth reductive removal of fluoride from the dearomatized intermediate, and (3) acid-promoted cyclization/aromatization. Mechanistic investigations revealed important characteristic reactivity of polyfluorophenols in the present system. Some of the fluorinated benzofuran products were transformed by utilizing the 2-methylsulfanyl moieties.
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