Oxidative Cleavage of Alkenes by Photosensitized Nitroarenes

摘要

Oxidative cleavage of alkenes into carbonyl molecules mainly relies on either ozonolysis or Le-mieux-Johnson oxidation involving high valent transition metal oxides. Safety, technical concerns and highly oxidizing conditions of both these procedures limited their adoption in streamlined synthesis. Like ozone, photosensitized nitroarenes can deliver similar types of [3+2] cycloaddition products with alkenes through biradical formation and the resulting "N-doped" ozo-nides can safely be converted to the corresponding carbonyl compounds through hydrolysis. The high prevalence of nitroarenes with diverse electronic and steric profiles combined with the mild oxidizing power allow to modulate site-selectivity and tolerate highly sensitive functional groups ideal for application in complex molecular setup.