Photoinduced-electron-transfer chemistry: from studies on PET processes to applications in natural product synthesis.
The application of photoinduced electron transfer (PET) for the construction of heterocyclic ring systems is an appealing route in synthetic organic photochemistry. Electronically excited carbonyl chromophors in ketones, aldehydes, amides, or imides are strong electron acceptors that oxidize alkenes, amines, thioethers, or carboxylates. In subsequent steps, the radical anions formed thereof either are operating as secondary electron donors and initiate a photon-driven chain reaction or combine with electrophilic species and form products. These reactions are applied in the synthesis of heterocyclic compounds. The basic structures of these target molecules are bicyclic tertiary amines from the pyrrolizidine, benzopyrrolizidine, and indolizidine families, cyclic oligopeptides, macrocyclic ring systems, and many more.
Griesbeck
Axel G
AG
Institute of Organic Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.
Hoffmann
Norbert
N
Warzecha
Klaus-Dieter
KD
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D004579:Electron Transport; D005609:Free Radicals; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007094:Imides / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000737:chemistry; D010777:Photochemistry; D017785:Photons; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013440:Sulfides / Q000737:chemistry
D000447:Aldehydes; D000475:Alkenes; D000577:Amides; D000588:Amines; D001688:Biological Products; D002264:Carboxylic Acids; D005609:Free Radicals; D006571:Heterocyclic Compounds; D007094:Imides; D007212:Indolizines; D007659:Ketones; D010456:Peptides, Cyclic; D011763:Pyrrolizidine Alkaloids; D013440:Sulfides