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 38 条
  • [1] Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/NCHEM.1222, 10.1038/nchem.1222]
  • [2] Vicinal difunctionalization of carbon-carbon double bond for the platform synthesis of trifluoroalkyl amines
    Beke, Ferenc
    Meszaros, Adam
    Toth, Agnes
    Botlik, Bence Bela
    Novak, Zoltan
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)
  • [3] Copper in cross-coupling reactions - The post-Ullmann chemistry
    Beletskaya, IP
    Cheprakov, AV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
  • [4] Brckner M., 2010, Organic Mechanisms: Reactions, Stereochemistry and Synthesis
  • [5] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS
    BUNNETT, JF
    ZAHLER, RE
    [J]. CHEMICAL REVIEWS, 1951, 49 (02) : 273 - 412
  • [6] New N- and O-arylations with phenylboronic acids and cupric acetate
    Chan, DMT
    Monaco, KL
    Wang, RP
    Winters, MP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
  • [7] Concerted nucleophilic aromatic substitution with 19F- and 18F-
    Eumann, Constanze N. N.
    Hooker, Jacob M.
    Ritter, Tobias
    [J]. NATURE, 2016, 534 (7607) : 369 - 373
  • [8] PALLADIUM-CATALYZED AROMATIC AMINATIONS WITH IN-SITU GENERATED AMINOSTANNANES
    GURAM, AS
    BUCHWALD, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) : 7901 - 7902
  • [9] EFFECTS OF CRYPTANDS AND ACTIVATION OF BASES .7. REDUCTION OF PHENYL HALIDES BY POTASSIUM HYDRIDE
    HANDEL, H
    PASQUINI, MA
    PIERRE, JL
    [J]. TETRAHEDRON, 1980, 36 (22) : 3205 - 3208
  • [10] A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS
    HANSCH, C
    LEO, A
    TAFT, RW
    [J]. CHEMICAL REVIEWS, 1991, 91 (02) : 165 - 195