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.

引用

页数：8

共 50 条

[31] External-Oxidant-Free Electrochemical Oxidative Trifluoromethylation of Arenes Using CF3SO2Na as the CF3 Source
Deng, Yong
Lu, Fangling
You, Siqi
Xia, Tianrui
Zheng, Yifan
Lu, Cuifen
Yang, Guichun
Chen, Zuxing
Gao, Meng
Lei, Aiwen
CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (08) : 817 - 820
[32] STRUCTURES OF (CF3)2O, (CF3)2O2 AND (CF3)2O3, DETERMINED BY ELECTRON DIFFRACTION ON VAPORS
HILDERBR.R
BAUER, SH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1969, (SEP): : P229 - &
[33] PREPARATION AND SPECTROSCOPIC CHARACTERIZATION OF CF3-SUBSTITUTED AMIDES, PHOSPHIDES, AND ARSENIDES, M(CF3)2-, P(CF3)2-, AS(CF3)2-
MINKWITZ, R
LIEDTKE, A
INORGANIC CHEMISTRY, 1989, 28 (09) : 1627 - 1630
[34] PREPARATION AND CHARACTERIZATION OF TRIPHOSPHOLENE COMPLEXES OF ZEROVALENT PLATINUM - CRYSTAL AND MOLECULAR-STRUCTURE OF [PT((CF3)P(CF3)PP(CF3)PC(CF3)=C(CF3))(PPH3)2]
PHILLIPS, IG
BALL, RG
CAVELL, RG
INORGANIC CHEMISTRY, 1987, 26 (24) : 4074 - 4079
[35] PREPARATION AND PROPERTIES OF BIS-TRIS(TRIFLUOROMETHYL)GERMYL CHALCOGENIDES - (CF3)3GE-TE-GE(CF3) (CF3)GE-3-O-GE(CF3)3, NCF3)GE-3-S-GE(CF3), (CF3), (CF3)GE-3-SE-GE(CF3)3 MOLECULAR-STRUCTURE OF [(CF3)3GE]O-2
EUJEN, R
LAUFS, FE
OBERHAMMER, H
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1988, 561 (06): : 82 - 98
[36] ANALYSIS OF (CF3)2CNH AND (CF3)2CND OSCILLATING SPECTRA
TREPALIN, SV
AKSINENKO, AY
SOKOLOV, VB
ZHURNAL FIZICHESKOI KHIMII, 1990, 64 (08): : 2045 - 2049
[37] Nucleophilic trifluoromethylation of cyclic imides using (trifluoromethyl) trimethylsilane CF3SiMe3
Hoffmann-Röder, A
Seiler, P
Diederich, F
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (16) : 2267 - 2269
[38] A mild and fast continuous-flow trifluoromethylation of coumarins with the CF3 radical derived from CF3SO2Na and TBHP
Zhang, Xiaodan
Huang, Ping
Li, Yaming
Duan, Chunying
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (44) : 10917 - 10922
[39] NUCLEOPHILIC TRIFLUOROMETHYLATION WITH THE REAGENT COMBINATION (ET2N)3P/CF3BR
RUPPERT, I
JOURNAL OF FLUORINE CHEMISTRY, 1985, 29 (1-2) : 98 - 98
[40] [Me3Si(CF3)F]- and [Me3Si(CF3)2]-:: Reactive intermediates in fluoride-initiated trifluoromethylation with Me3SiCF3 -: An NMR study
Maggiarosa, N
Tyrra, W
Naumann, D
Kirij, NV
Yagupolskii, YL
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (15) : 2252 - 2253

← 1 2 3 4 5 →