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

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

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...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2024-06, Vol.29 (12), p.2905
Hauptverfasser: Chen, Dingben, Huang, Ling, Liang, Mingyu, Chen, Xiaojing, Cao, Dongdong, Xiao, Pan, Ni, Chuanfa, Hu, Jinbo
Format: Artikel
Sprache:eng
Schlagworte:
1,6-nucleophilic addition
Catalysis
CsF/18-crown-6
difluoromethylation
Investigations
Me3SiCF2H/Me3SiCF3
Pesticides
Phenols
Reagents
Solvents
Temperature
trifluoromethylation
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Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29122905