Direct Amination of Azoles via Catalytic C-H, N-H Coupling

被引:345
作者
Monguchi, Daiki [1 ]
Fujiwara, Taiki [1 ]
Furukawa, Hirotoshi [1 ]
Mori, Atsunori [1 ]
机构
[1] Kobe Univ, Dept Sci & Chem Engn, Kobe, Hyogo 6578501, Japan
关键词
BOND FORMATION; DIRECT ARYLATION; ARYL HALIDES; EFFICIENT; FUNCTIONALIZATION; 2,5-DIARYLTHIAZOLE; BROMOTHIOPHENE; DERIVATIVES; AMIDATION; ACTIVATOR;
D O I
10.1021/ol900298e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.
引用
收藏
页码:1607 / 1610
页数:4
相关论文
共 60 条
  • [1] One-step synthesis of 2-arylbenzothiazole ('BTA') and -benzoxazole precursors for in vivo imaging of β-amyloid plaques
    Alagille, D
    Baldwin, RM
    Tamagnan, GD
    [J]. TETRAHEDRON LETTERS, 2005, 46 (08) : 1349 - 1351
  • [2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [3] Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions
    Arai, Nobumichi
    Miyaoku, Takayuki
    Teruya, Shota
    Mori, Atsunori
    [J]. TETRAHEDRON LETTERS, 2008, 49 (06) : 1000 - 1003
  • [4] Palladium-catalyzed intramolecular CH arylation of five-membered N-heterocycles
    Arai, Nobumichi
    Takahashi, Masabumi
    Mitani, Makoto
    Mori, Atsunori
    [J]. SYNLETT, 2006, (18) : 3170 - 3172
  • [5] Copper-Nitrene Complexes in Catalytic C-H Amination
    Badiei, Yosra M.
    Dinescu, Adriana
    Dai, Xiliang
    Palomino, Robert M.
    Heinemann, Frank W.
    Cundari, Thomas R.
    Warren, Timothy H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) : 9961 - 9964
  • [6] Copper-mediated C-H bond arylation of arenes with arylboronic acids
    Ban, Ikuya
    Sudo, Tomoko
    Taniguchi, Tadashi
    Itami, Kenichiro
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3607 - 3609
  • [7] Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides
    Bellina, Fabio
    Calandri, Chiara
    Cauteruccio, Silvia
    Rossi, Renzo
    [J]. TETRAHEDRON, 2007, 63 (09) : 1970 - 1980
  • [8] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [9] Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
  • [10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791