Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions

We disclose herein an efficient photochemical formal [3+2+1] annulation strategy for the transformation of diazocarbonyl compounds into various fluorinated nitrogen-containing heterocycles. This transformation is characterized by reacting fluoroalkyl radicals with alpha-diazoketones, which are used as infrequent denitrogenated synthons under visible light. Moreover, a wide range of N-heterocycles containing precious CF3 and perfluoroalkylated groups are constructed in moderate to good yields. Notably, this photochemical strategy may provide a fruitful path for the synthesis of complex organofluorides via diazo/fluorine/radical chemistry.

Automated summary

An efficient photochemical strategy for the synthesis of fluorinated nitrogen-containing heterocycles from diazocarbonyl compounds is disclosed. This transformation involves the reaction of fluoroalkyl radicals with alpha-diazoketones under visible light. A wide range of N-heterocycles containing CF3 and perfluoroalkylated groups are successfully constructed in moderate to good yields. This photochemical strategy may serve as a valuable method for the synthesis of complex organofluorides via diazo/fluorine/radical chemistry.