Exploiting Iminoquinones as Electrophilic at Nitrogen “N+” Synthons for C–N Bond Construction

Autor: Mori-Quiroz, Luis M., Comadoll, Chelsea G., Super, Jonathan E., Clift, Michael D.
Zdroj: Organic Letters; 20210101, Issue: Preprints
Abstrakt: New methods for C–N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situvia the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.
Databáze: Supplemental Index