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

Thomas Delouche; Abdoul Gadiry-Diallo; Thierry Besson; Sensuke Ogoshi; Corinne Fruit

doi:10.1055/a-2054-0482

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(21): 3670-3684
DOI: 10.1055/a-2054-0482

special topic

C–H Bond Functionalization of Heterocycles

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

Autor*innen

Thomas Delouche

^aUniv Rouen Normandie, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
Abdoul Gadiry-Diallo

^aUniv Rouen Normandie, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
Thierry Besson

^aUniv Rouen Normandie, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
Sensuke Ogoshi

^bDepartment of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Corinne Fruit ∗

^aUniv Rouen Normandie, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France

Abstract

Alle Artikel dieser Rubrik

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

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Referenzen

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