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C–H Sulfonylation via 1,3-Rearrangement of Sulfonyl Group in N‑Protected 3‑Bis-sulfonimidoindole Derivatives Using Fluorine Reagent

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journal contribution
posted on 01.04.2020, 12:11 by Kazuhiro Watanabe, Katsuhiko Moriyama
A C–H sulfonylation of N-protected 3-bis-sulfonimidoindole derivatives via a 1,3-rearrangement of a sulfonyl group on a bis-sulfonimide moiety using tetra-n-butylammonium fluoride (TBAF) was developed to provide 2-sulfonyl-3-sulfonamidoindole derivatives in high yields as a novel Csp2–H functionalization of heterocycles. The rearrangement of the sulfonyl group proceeded through an intermolecular addition of the desorbed sulfinyl ion from the bis-sulfonimide moiety in the substrate.