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
收藏
页数：8
相关论文
共 50 条
  • [41] THE INTERACTION OF CF3 RADICALS AND CF3 RADICAL PRECURSORS WITH SIO2 SURFACES
    MCFEELY, FR
    YARMOFF, JA
    TALEBIBRAHIMI, A
    BEACH, DB
    SURFACE SCIENCE, 1988, 206 (03) : 371 - 378
  • [42] [H(OEt2)2]+ and [Ph3C]+ salts of the borate anions [B(CF3)4]-, [(CF3)3BCN]-, and [B(CN)4]-
    Finze, M
    Bernhardt, E
    Berkei, M
    Willner, H
    Hung, J
    Waymouth, RM
    ORGANOMETALLICS, 2005, 24 (21) : 5103 - 5109
  • [43] REACTIONS OF CIS[OCH(CF3)2]3 AND S[OCH(CF3)2]2 WITH PHOSPHORUS (III) DERIVATIVES
    ROSCHENTHALER, GV
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1981, 479 (08): : 158 - 164
  • [44] OXIDATIVE FLUORINATION OF (CF3)(R)CS(O2)C(CF3)(R)S (R=CF3, CL) AND THE CRYSTAL-STRUCTURE OF (CF3)(CL)CS(O2)C(CF3)(CL)SF+ASF6-
    MINKWITZ, R
    BACK, B
    PREUT, H
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1994, 620 (06): : 1125 - 1131
  • [45] PREPARATION, STRUCTURE, AND PROPERTIES OF [NI(S2C2(CF3)2)2]- AND [NI(SE2C2(CF3)2)2]- SALTS WITH SMALL CATIONS
    HARRIS, NJ
    UNDERHILL, AE
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1987, (07): : 1683 - 1685
  • [46] Study on the Degradation of the Highly Reactive Hypervalent Trifluoromethylation Iodine Reagent PhI(OAc)(CF3)
    Zhu, Hui
    Zhang, Shusheng
    Wang, Haoyang
    Xu, Bin
    Guo, Yinlong
    CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (12) : 1365 - 1370
  • [47] INFRARED AND RAMAN SPECTRA OF (CF3)2C=C=O, (CF3)2C=N=N AND (CF3)2C=NH
    MILLER, FA
    KIVIAT, FE
    SPECTROCHIMICA ACTA PART A-MOLECULAR SPECTROSCOPY, 1969, A 25 (09): : 1577 - &
  • [48] Electrophilic trifluoromethylation of simple inorganic salts:: a one step route to trifluoromethylnitromethane, CF3NO2
    Muralidharan, K
    Chakraborty, R
    Shreeve, JM
    JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (12) : 1967 - 1968
  • [49] New Avenues in Copper-Mediated Trifluoromethylation Reactions Using Fluoroform as the CF3 Source
    Yang, Xinkan
    Tsui, Gavin Chit
    SYNLETT, 2022, 33 (08) : 713 - 720
  • [50] PREPARATION, STRUCTURE AND PROPERTIES OF [NI(S2C2(CF3)2)2]- SALTS
    HARRIS, NJ
    UNDERHILL, AE
    SYNTHETIC METALS, 1987, 19 (1-3) : 959 - 962
12345