The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 29, 2025

An efficient and regioselective method for the intermolecular hydrofunctionalization of enamides N-vinyl azoles has been developed, enabling formation diverse C-S, C-O, C-N, C-C bonds. This transition-metal-free, additive-free, Brønsted acid-free protocol employs hexafluoroisopropanol (HFIP) as sole reagent, which plays a dual role: iminium carbocation intermediate facilitating nucleophile generation through its hydrogen-bonding network. The reaction demonstrates exceptional substrate versatility, accommodating thiophenols, alcohols, heterocyclic amines, well NH-free indoles, pyrroles, carbazoles nucleophiles, proceeding via Markovnikov-selective pathway. is general simple with broad compatibility.

Язык: Английский