Relay Cu(I)/Bronsted Base Catalysis for Phospha-Michael Addition/5-exo-dig Cyclization/Isomerization of in situ Formed aza-Alkynyl o-quinone methides with P(O)-H compounds to C3-Phosphorylated Indoles

A relay Cu(I)/Bronsted base catalyzed one-pot phospha-Michael addition/5-exo-dig cyclization/isomerization of in situ generated aza-alkynyl o-quinone methides (N-o-AQMs) from 1-(o-aminophenyl)prop-2-ynols with P(O)-compounds has been established to afford C3-phosphorylated indoles. It demonstrates that the 1,4-conjugate addition adduct from N-o-AQMs could undergo further cyclization with the tethered alkyne moiety to afford N-heterocyclic compounds.

Automated summary

The one-pot phospha-Michael addition/5-exo-dig cyclization/isomerization reaction catalyzed by relay Cu(I)/Brønsted base successfully synthesized C3-phosphorylated indoles from in situ generated aza-alkynyl o-quinone methides (N-o-AQMs) and P(O)-compounds. The study demonstrated that the 1,4-conjugate addition adduct from N-o-AQMs could undergo further cyclization with the tethered alkyne moiety to afford N-heterocyclic compounds.