Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2•bPY

被引：3
|
作者：
Pan, Shitao [1 ]
Wang, Xiu [1 ]
Ni, Chuanfa [1 ]
Hu, Jinbo [1 ]
机构：
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,Key Lab Organofluorine C, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2021年 / 100卷
基金：
中国国家自然科学基金;
关键词：
(Trifluoromethyl)zinc reagent; Trifluoromethylation; Nucleophilic addition; Azinium salts; COPPER-CATALYZED TRIFLUOROMETHYLATION; FLUORINE; SUBSTITUTION; ALDIMINES; HYDROGEN; ALKYNES; AZINES; ARYL;
D O I：
10.1016/j.tet.2021.132477
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(Trifluoromethyl)zinc complexes have been widely used in metal-mediated trifluoromethylation reactions. However, direct nucleophilic addition with a (trifluoromethyl)zinc complex is rare. In this article, we describe an unprecedented trifluoromethylation of azinium salts using Zn(CF3)(2)center dot bpy as CF3 source, giving 1-(4-methoxybenzyl)-2-(trifluoromethyl)-1,2-dihydroquinolines as products. The latter species were further transformed to 2-trifluoromethylquinolines under oxidative conditions. This work also shows that ligands play an important role in tuning the reactivity of (trifluoromethyl)zinc complexes. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：8
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