Here, ten guidelines are presented for a standardized definition of type I and II photosensitized oxidation reactions. Because of varied notions of reactions mediated by photosensitizers, a checklist of recommendations is provided for their definitions. Type I and type II photoreactions are oxygen-dependent and involve unstable species such as the initial formation of radical cation or neutral radicals from the substrates and/or singlet oxygen (1O2 1Δg) by energy transfer to molecular oxygen. In addition, superoxide anion radical (O2•−) can be generated by a charge transfer reaction involving O2 or more likely indirectly as the result of O2-mediated oxidation of the radical anion of type I photosensitizers. In subsequent reactions, O2•− may add and/or reduce a few highly oxidizing radicals that arise from the deprotonation of the radical cations of key biological targets. O2•− can also undergo dismutation into H2O2, the precursor of the highly reactive hydroxyl radical (•OH) that may induce delayed oxidation reactions in cells. In the second part several examples of type I and type II photosensitized oxidation reactions are provided to illustrate the complexity and the diversity of the degradation pathways of mostly relevant biomolecules upon one-electron oxidation and singlet oxygen reactions.

This Review describes singlet oxygen ((1)O2) in the organic synthesis of targets on possible (1)O2 biosynthetic routes. The visible-light sensitized production of (1)O2 is not only useful for synthesis; it is extremely common in nature. This Review is intended to draw a logical link between flow and batch reactions-a combination that leads to the current state of (1)O2 in synthesis.