jo0c00172_si_001.pdf (22.6 MB)
Consecutive Aryne Generation Strategy for the Synthesis of 1,3-Diarylpyrazoles
journal contribution
posted on 2020-02-24, 14:35 authored by Tsuneyuki Kobayashi, Takamitsu Hosoya, Suguru YoshidaAn efficient method for the synthesis
of diverse 1,3-diarylpyrazoles
via consecutive aryne generation has been developed. The bisaryne
precursors bearing o-iodo- and o-silylaryl triflate moieties were prepared by sequential Suzuki–Miyaura
and Chan–Lam–Evans cross-coupling reactions. The selective
generation of the first aryne triggered by a silylmethyl Grignard
reagent followed by the second aryne generation mediated by a fluoride
ion allowed for the synthesis of diverse multisubstituted 1,3-diarylpyrazoles
in a modular synthetic manner with various arynophiles.