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

被引:1
作者
Delouche, Thomas [1 ]
Gadiry-Diallo, Abdoul [1 ]
Besson, Thierry [1 ]
Ogoshi, Sensuke [2 ]
Fruit, Corinne [1 ]
机构
[1] Univ Rouen Normandie, INSA Rouen, CNRS, COBRA,UMR 6014, F-76000 Rouen, France
[2] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 21期
关键词
visible light; perfluoroalkylation; quinazolin-4(3 H )-ones; thiazoloquinazolinone; C-H functionalization; metal-free; ONE-POT SYNTHESIS; CATALYZED PERFLUOROALKYLATION; PENTAFLUOROETHYL COPPER; NEXT-GENERATION; ARYL IODIDES; FLUOROALKYLATION; TRIFLUOROMETHYLATION; FUNCTIONALIZATION; DERIVATIVES; INHIBITORS;
D O I
10.1055/a-2054-0482
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:3670 / 3684
页数:15
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