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

Abstract

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.