Carbazole Annulation via Cascade Nucleophilic Addition-Cyclization Involving 2-(Silyloxy)pentadienyl Cation.
We report a new strategy toward the synthesis of highly functionalized carbazoles via 2-(silyloxy)pentadienyl cation intermediates, which were generated upon ionization of vinyl-substituted α-hydroxy silyl enol ethers under Brønsted acid catalysis. These electrophilic species were found to readily undergo cascade reactions with substituted indoles to generate carbazole molecular scaffolds in good yields via a sequence of regioselective nucleophilic addition, followed by intramolecular dehydrative cyclization.
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Jacob R
JR
Stepherson
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Caitlan E
CE
Ayala
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Thomas H
TH
Tugwell
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Jeffrey L
JL
Henry
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Frank R
FR
Fronczek
Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Rendy
R
Kartika