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Beautiful Chemistry-Photoinduced Alkene Cleavage Using Nitroarenes

  The oxidative cleavage of olefins is an important transformation in organic synthesis to obtain carbonyl functional groups such as ketones and aldehydes. The current used approaches, such as ozonolysis and Lemieux-Johnson Oxidation suffer from many significant limitations. Thus the development of a mild, general, and practical approach is still highly warranted. Oxidative Cleavage of Alkenes [1] A recent report from Parasram group (J. Am. Chem. Soc. 2022, 144, 15437.) indicated a visible light-induced anaerobic cleavage of alkenes by using economical and bench-stable nitroarenes as oxygen transfer reagents. The authors used 4-fluorostyrene as the control olefin to optimize the reaction conditions. They found 4-CN-nitrobenzene was the best nitroarene for such transformations. A few other nitroarenes bearing strong electron-withdrawing group gave satisfactory results, while nitroarene bearing electron-donating group gave poor conversion. Optimization of reaction condition [1] By us...