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

Abstract

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.

Key words

visible light - perfluoroalkylation - quinazolin-4(3H)-ones - thiazoloquinazolinone - C–H functionalization - metal-free

Publication History

Received: 31 January 2023

Accepted after revision: 14 March 2023

Accepted Manuscript online:
14 March 2023

Article published online:
11 April 2023

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