Hydrogen-Bonding Network-Enabled Terminal Selective Heteroarylation of Allenamides in Hexafluoroisopropanol

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 21, 2025

Hexafluoroisopropanol (HFIP)-mediated terminal selective heteroarylation of allenamides has been accomplished through H-bonding network-enabled substrate activation in a robust fashion. This strategy features cascade process involving sequential nucleophilic addition followed by electrophilic heteroaromatic substitution and is well suited for late-stage functionalization complex bioactive molecules. The elucidation the underlying mechanism was achieved comprehensive combination several control experiments, kinetic studies, isotopic labeling isolation HFIP-allenamide intermediate adduct.

Язык: Английский

HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature

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

Опубликована: Март 25, 2025

Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo[1,2-a]pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In method, HFIP, besides offering hydrogen bonding alcohol, also stabilizes resultant carbocation, thus forming product. This method enables straightforward synthesis 1,3-enynes. The current offers a large substrate diversity good to excellent yields. We demonstrated gram-scale modifications.

Язык: Английский

HFIP-Mediated Cascade Aminomethylation and Intramolecular Cyclization of Allenamides with N,O-Acetals to Access Tetrahydro-β-carboline Derivatives

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A cascade of two C–C bond forming reactions promoted alone by HFIP is described delivering tetrahydro-β-carboline derivatives embedded with an allylic amine functionality.

Язык: Английский