Low energy light-triggered oxidative cleavage of olefins

A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygen-mediated cleavable linker. Low intensity light of 200 mW/cm2 was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.