Dynamic Dual Role as Cationic Cu + and Cu Alkoxide in Cu-Catalyzed Dearomative Cascade Reactions
Abstract
High Resolution Image Download MS PowerPoint Slide The reactions of N -alkoxyanilines, which have an electron-donating group at the ortho position, with alcohols in the presence of cationic NHC-Cu and alkoxide cocatalysts afforded dearomative 1,4-cyclohexadiene derivatives in good yields with high product selectivities. The Cu cocatalyst dynamically plays a dual role as a Lewis acidic catalyst to promote the [1,3]-alkoxy rearrangement and a Lewis base catalyst to facilitate the 1,4-addition of the alcohol to the ortho -quinol imine intermediate through the formation of alkoxycopper species.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Catalytic C–H Functionalization Methods
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1264–1269
- Publication date
- 21 January 2026
- Language
- EN