Light-induced carbocyclization of iodoalkenes

Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates

“…3,133,134 Substituted phenanthrenes have been prepared in high yields by exploiting this approach. 135 In a recent application, vinyl radicals were obtained from α-bromocinnamates or -chalcones employing a visible light photoredox strategy (Scheme 46). Monoelectronic reduction of the starting substrate 115 and subsequent detachment of the bromide anion afforded vinyl radical 116 • that, upon addition onto heteroarenes (such as furan) and ensuing cyclization, gave intermediate 117 • .…”

“…Vinyl radicals are widely used as intermediates in ring formation, and different generation strategies have been developed. One of the approaches involved photohomolysis of vinyl halides, although heterolytic cleavage of the C-X bond often competed. ,, Substituted phenanthrenes have been prepared in high yields by exploiting this approach . In a recent application, vinyl radicals were obtained from α-bromo-cinnamates or -chalcones employing a visible light photoredox strategy (Scheme ).…”

A new era for homolytic aromatic substitution: replacing Bu3SnH with efficient light-induced chain reactions

“…It is well-established that UV-light can allow HAS to occur in the absence of radical initiators, [29][30][31][32][33][34][35][36][37] particularly aryl radical substitutions, which can be superior to those using Bu 3 SnH. 36 Benzimidazol-2-yl radicals readily cyclize onto aromatics with best yields achieved in the presence of a small quantity of sodium carbonate required to quench HI (Scheme 9).…”

Recent Developments in Radical‐Mediated Transformations of Organohalides

“…One of the strategies concerned vinyl halide photohomolysis, even though corban–halogen bond scission often competed . Phenanthrene derivatives were synthesized in good yields by developing this strategy . In a current report, α‐bromocinnamate or ‐chalcone generated the vinyl radical through a visible light photoredox approach (Scheme ).…”