Directed nucleophilic aromatic substitution reaction

被引:0
|
作者
Nitta, Yasuyuki [1 ]
Nakashima, Yusei [1 ]
Sumimoto, Michinori [1 ]
Nishikata, Takashi [1 ]
机构
[1] Yamaguchi Univ, Grad Sch Sci & Engn, 2-16-1 Tokiwadai, Ube, Yamaguchi 7558611, Japan
关键词
CROSS-COUPLING REACTIONS; DEOXYFLUORINATION; HALIDES; AMINE;
D O I
10.1039/d4cc04912h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, we discovered a directed nucleophilic aromatic substitution reaction, "directed SNAr (dSNAr)," in the reaction of ortho-iodobezamides and amine in the presence of pyridine. The reaction proceeded ortho-specifically and did not require a strong electron-withdrawing group on the arene substrate. Most reactions proceeded at room temperature in the presence of Py, and a wide range of amine nucleophiles can be applied. Furthermore, the reactions with benzamide substituted with multiple halogens were found to be 100% ortho-selective.
引用
收藏
页码:14284 / 14287
页数:4
相关论文
共 50 条
  • [21] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS
    BUNNETT, JF
    ZAHLER, RE
    CHEMICAL REVIEWS, 1951, 49 (02) : 273 - 412
  • [22] Nucleophilic aromatic substitution with dialkoxycarbenes
    McMaster Univ, Hamilton, Canada
    Can J Chem, 10 (1331-1335):
  • [23] Development and application of ester-mediated nucleophilic aromatic substitution reaction
    Hattori, T
    Miyano, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (02) : 121 - 131
  • [24] The reaction catalyzed by tetrachlorohydroquinone dehalogenase does not involve nucleophilic aromatic substitution
    Kiefer, PM
    McCarthy, DL
    Copley, SD
    BIOCHEMISTRY, 2002, 41 (04) : 1308 - 1314
  • [25] New Highly Stable Metallabenzenes via Nucleophilic Aromatic Substitution Reaction
    Lin, Ran
    Zhang, Hong
    Li, Shunhua
    Wang, Jiani
    Xia, Haiping
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4223 - 4231
  • [26] Microwave assisted aromatic nucleophilic substitution reaction under solventless condition
    Rebeiro, GL
    Khadilkar, BM
    SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1405 - 1410
  • [27] Development and application of ester-mediated nucleophilic aromatic substitution reaction
    Tohoku Univ, Sendai, Japan
    Yuki Gosei Kagaku Kyokaishi, 2 (121-131):
  • [28] AROMATIC NUCLEOPHILIC-SUBSTITUTION .15. REACTION OF PERFLUOROINDAN AND PERFLUOROTETRALIN WITH NUCLEOPHILIC-REAGENTS
    FURIN, GG
    MALYUTA, NG
    PLATONOV, VE
    YAKOBSON, GG
    ZHURNAL ORGANICHESKOI KHIMII, 1974, 10 (04): : 830 - 838
  • [29] Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution
    Cardenas, Mariel M.
    Toenjes, Sean T.
    Nalbandian, Christopher J.
    Gustafson, Jeffrey L.
    ORGANIC LETTERS, 2018, 20 (07) : 2037 - 2041
  • [30] Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution
    Sadowsky, Daniel
    McNeill, Kristopher
    Cramer, Christopher J.
    ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2014, 48 (18) : 10904 - 10911