1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6-Reference-Cited by-同舟云学术

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

Published:2024-06-19 Issue:12 Volume:29 Page:2905
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Chen Dingben¹²^ORCID,Huang Ling¹,Liang Mingyu¹,Chen Xiaojing¹,Cao Dongdong¹,Xiao Pan²³,Ni Chuanfa²,Hu Jinbo²³^ORCID

Affiliation:

1. School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China

2. 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

3. School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China

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.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Strategic Priority Research Program of the Chinese Academy of Sciences

Natural Science Foundation of Shandong Province

Natural Science Foundation of Zhejiang Province

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/12/2905/pdf

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