Iron-Catalyzed Stereoselective Synthesis of Dihydrobenzofurans from O -Tethered Enynes and DDQ-Mediated Oxidative Annulation to Dibenzofurans
Abstract
Abstract Iron-catalyzed stereoselective cyclization of O-tethered enynes has been developed for facile access of 2-methyl-2,3-dihydrobenzofurans in good to excellent yields. The transformation proceeds through an acetyl chloride-assisted intramolecular addition under mild conditions, generating alkenyl chloride intermediates with exclusive Z-selectivity. More than 99% deuterium incorporation was observed when D2O was used instead of H2O. Subsequent DDQ-mediated oxidative aromatization furnishes dibenzofuran-2,3-dicarbonitrile derivatives in excellent yields via a dehydrogenative annulation pathway. This operationally simple and ligand-free method offers a cost-effective general method to afford functionalized 2,3-dihydrobenzofurans and dibenzofuran-2,3-dicarbonitriles.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Cross-Coupling Reactions
Catalytic Alkyne Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 26
- Pages
- 8247–8252
- Publication date
- 18 June 2026
- Language
- EN