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

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.

本研究开发了一种以四正丁基氟化铵（tetra-n-butylammonium fluoride, TBAF）为试剂，依托双磺酰亚胺基团上磺酰基的1,3-重排过程的N-保护3-双磺酰亚胺基吲哚衍生物的C-H磺酰化反应，该反应可高产率制备2-磺酰基-3-磺酰胺基吲哚衍生物，属于一类新型的杂环Csp²-H官能化策略。该磺酰基的重排过程经由底物中双磺酰亚胺基团脱附得到的亚磺酰离子发生分子间加成得以进行。