HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N ‑Vinyl Azoles
| Title: | HFIP-Promoted Regioselective Hydrofunctionalization of Enamides and N ‑Vinyl Azoles |
|---|---|
| Authors: | Susanta Patra; Satyajit Samanta; Vishal Talukdar; Parthasarathi Das |
| Publication Year: | 2025 |
| Subject Terms: | Biophysics; Biochemistry; Genetics; Evolutionary Biology; Computational Biology; Biological Sciences not elsewhere classified; Chemical Sciences not elsewhere classified; iminium carbocation intermediate; facilitating nucleophile generation; broad substrate compatibility; >‑ vinyl azoles; >- vinyl azoles; selective hydrofunctionalization pathway; diverse c –; promoted regioselective hydrofunctionalization; >- free indoles; c – n; c –; intermolecular hydrofunctionalization; regioselective method; n |
| Description: | An efficient and regioselective method for the intermolecular hydrofunctionalization of enamides and N -vinyl azoles has been developed, enabling the formation of diverse C–S, C–O, C–N, and C–C bonds. This transition-metal-free, additive-free, and Brønsted acid-free protocol employs hexafluoroisopropanol (HFIP) as the sole reagent, which plays a dual role: formation of iminium carbocation intermediate and facilitating nucleophile generation through its hydrogen-bonding network. The reaction demonstrates exceptional substrate versatility, accommodating thiophenols, alcohols, heterocyclic amines, as well as NH -free indoles, pyrroles, and carbazoles as nucleophiles, proceeding via a Markovnikov-selective hydrofunctionalization pathway. The protocol is general and simple with broad substrate compatibility. |
| Document Type: | article in journal/newspaper |
| Language: | unknown |
| DOI: | 10.1021/acs.joc.5c00378.s001 |
| Availability: | https://doi.org/10.1021/acs.joc.5c00378.s001; https://figshare.com/articles/journal_contribution/HFIP-Promoted_Regioselective_Hydrofunctionalization_of_Enamides_and_i_N_i_Vinyl_Azoles/28892863 |
| Rights: | CC BY-NC 4.0 |
| Accession Number: | edsbas.7E69C663 |
| Database: | BASE |