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1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

Authors :
Dingben Chen
Ling Huang
Mingyu Liang
Xiaojing Chen
Dongdong Cao
Pan Xiao
Chuanfa Ni
Jinbo Hu
Source :
Molecules, Vol 29, Iss 12, p 2905 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.

Details

Language :
English
ISSN :
14203049
Volume :
29
Issue :
12
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.070b5fb724e44b36909f962e7e864f75
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules29122905