Photoredox-Catalyzed Divergent Radical Cascade Annulations of 1,6-Enynes via Pyridine N-Oxide-Promoted Vinyl Radical Generation

B Wang, J Singh, Y Deng - Organic letters, 2023 - ACS Publications
B Wang, J Singh, Y Deng
Organic letters, 2023ACS Publications
The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1, 6-
enynes were developed. A series of cyclopropane-fused hetero-and carbo-bicyclic, tricyclic,
and spiro-tetracyclic compounds were facilely synthesized from a broad scope of 1, 6-
enynes and 2, 6-lutidine N-oxide under mild and metal-free conditions with blue light-
emitting diode light irradiation. The cascade annulation reaction occurs with the
intermediacy of a β-oxyvinyl radical, which is produced from photocatalytically generated …
The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1,6-enynes were developed. A series of cyclopropane-fused hetero- and carbo-bicyclic, tricyclic, and spiro-tetracyclic compounds were facilely synthesized from a broad scope of 1,6-enynes and 2,6-lutidine N-oxide under mild and metal-free conditions with blue light-emitting diode light irradiation. The cascade annulation reaction occurs with the intermediacy of a β-oxyvinyl radical, which is produced from photocatalytically generated pyridine N-oxy radical addition to the carbon–carbon triple bond.
ACS Publications