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- Title
1,1,1,3,3,3-Hexafluoro-2-Propanol-Promoted Friedel–Crafts Reaction: Metal-Free Synthesis of C3-Difluoromethyl Carbinol-Containing Imidazo[1,2- a ]pyridines at Room Temperature.
- Authors
Gao, Juanjuan; Liu, Zhaowen; Guo, Xiaohua; Wu, Longhui; Chen, Zhixi; Yang, Kai
- Abstract
A facile and efficient method has been developed for the synthesis of C3-difluoromethyl carbinol-containing imidazo[1,2-a]pyridines at room temperature via the HFIP-promoted Friedel–Crafts reaction of difluoroacetaldehyde ethyl hemiacetal and imidazo[1,2-a]pyridines. This strategy could be applied to the direct C(sp2)-H hydroxydifluoromethylation of imidazo[1,2-a]pyridines and afford a series of novel difluoromethylated carbinols in good to satisfactory yields with 29 examples. Furthermore, gram-scale and synthetic transformation experiments have also been achieved, demonstrating its potential applicable value in organic synthesis. This green protocol has several advantages, including being transition metal- and oxidant-free, being carried out at room temperature, having high efficiency, and having a wide substrate scope.
- Subjects
IMIDAZOPYRIDINES; FRIEDEL-Crafts reaction; TEMPERATURE; ORGANIC synthesis
- Publication
Molecules, 2023, Vol 28, Issue 22, p7522
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28227522