Intramolecular electron transfer initiated cation and radical formation through carbon-carbon bond activation.
Radical cations can be formed in a spatially and temporally controlled manner by appending a sacrificial photooxidant to an easily oxidized substrate, leading to intramolecular electron transfer upon irradiation. The anthraquinone carboxyl group is an effective photooxidant that can promote single electron oxidation from an appended arene. The resulting intermediates undergo a cleavage reaction through carbon-carbon bond activation to provide either cations or radicals that react to form a range of products.
Tu
Wangyang
W
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Floreancig
Paul E
PE
D000880:Anthraquinones / Q000737:chemistry* / Q000528:radiation effects; D002244:Carbon / Q000737:chemistry*; D002412:Cations / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000880:Anthraquinones; D002412:Cations; D005609:Free Radicals; D002244:Carbon