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

Dingben Chen; Ling Huang; Mingyu Liang; Xiaojing Chen; Dongdong Cao; Pan Xiao; Chuanfa Ni; Jinbo Hu

doi:10.3390/molecules29122905

Molecules (Jun 2024)

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

Dingben Chen,
Ling Huang,
Mingyu Liang,
Xiaojing Chen,
Dongdong Cao,
Pan Xiao,
Chuanfa Ni,
Jinbo Hu

Affiliations

Dingben Chen: School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Ling Huang: School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Mingyu Liang: School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Xiaojing Chen: School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Dongdong Cao: School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Pan Xiao: Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
Chuanfa Ni: Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
Jinbo Hu: Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

DOI: https://doi.org/10.3390/molecules29122905
Journal volume & issue: Vol. 29, no. 12
p. 2905

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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