Photocatalyst-Free, Visible-Light-Mediated C-H Perfluoroalkylation of Quinazolin-4(3 H )-ones with perfluoroalkyl Iodides

A practical and sustainable photocatalyst-free protocol for photoinduced synthesis of perfluoroalkylated quinazolin-4(3H)-ones is described starting from quinazolin-4(3H)-ones. A wide range of substituted or fused-quinazolinones is found to be compatible, providing the corresponding mono-and bis-perfluoroalkylated compounds in moderate yields. This visible-light-mediated C-H perfluoroalkylation allows an environmentally friendly and straightforward access to an array of unprecedented functionalized quinazolinone scaffolds, presenting attractive features for drug discovery. Control experiments demonstrated that a radical mechanism is involved in the reaction mechanism.

Automated summary

A practical and sustainable protocol for the synthesis of perfluoroalkylated quinazolin-4(3H)-ones from quinazolin-4(3H)-ones is described. Various substituted or fused-quinazolinones are compatible, yielding mono- and bis-perfluoroalkylated compounds in moderate yields. This photocatalyst-free and visible-light-mediated C-H perfluoroalkylation offers an environmentally friendly approach to novel functionalized quinazolinone scaffolds with potential for drug discovery. Control experiments confirm the involvement of a radical mechanism.