Iridium-catalyzed direct borylation of five-membered heteroarenes by bis(pinacolato)diboron: Regioselective, stoichiometric, and room temperature reactions

被引：163
|
作者：
Ishiyama, T [1 ]
Takagi, J
Yonekawa, Y
Hartwig, JF
Miyaura, N
机构：
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido, Japan
[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2003年 / 345卷 / 9-10期
关键词：
boron; C-H activation; heterocycles; homogeneous catalysis; iridium;
D O I：
10.1002/adsc.200303058
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An iridium(I) complex generated from 1/2[Ir(OMe)(COD)](2) and 4,4'-di-tert-butyl-2,2'-bipyridine catalyzed the direct borylation of 2-substituted thiophenes, furans and pyrroles in stoichiometric amounts relative to bis(pinacolato)diboron in hexane at room temperature. The heteroarylboronates from regioselective C-H activation at the 5-position were formed in high yields. Similar borylations of unsubstituted heteroarenes with an equimolar amount of the diboron regioselectively provided 2,5-bis(boryl)heteroarenes.
引用
收藏
页码：1103 / 1106
页数：4
相关论文
共 31 条
  • [1] Iridium-catalyzed ortho-C-H Borylation of Aryl Ketones with Bis(pinacolato)diboron
    Itoh, Hiroshi
    Kikuchi, Takao
    Ishiyama, Tatsuo
    Miyaura, Norio
    CHEMISTRY LETTERS, 2011, 40 (09) : 1007 - 1008
  • [2] Iridium-catalyzed vinylic C-H borylation of cyclic vinyl ethers by bis(pinacolato)diboron
    Kikuchi, Takao
    Takagi, Jun
    Ishiyama, Tatsuo
    Miyaura, Norio
    CHEMISTRY LETTERS, 2008, 37 (06) : 664 - 665
  • [3] Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
    Takagi, J
    Sato, K
    Hartwig, JF
    Ishiyama, T
    Miyaura, N
    TETRAHEDRON LETTERS, 2002, 43 (32) : 5649 - 5651
  • [4] Iridium(I)-catalyzed C-H Borylation of α,β-Unsaturated Esters with Bis(pinacolato)diboron
    Sasaki, Ikuo
    Taguchi, Jumpei
    Doi, Hana
    Ito, Hajime
    Ishiyama, Tatsuo
    CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (09) : 1400 - 1405
  • [5] Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane
    Zhang, Sheng
    Yu, Xiaoqiang
    Feng, Xiujuan
    Yamamoto, Yoshinori
    Bao, Ming
    CHEMICAL COMMUNICATIONS, 2015, 51 (18) : 3842 - 3845
  • [6] Regioselective aromatic C-H silylation of five-membered heteroarenes with fluorodisilanes catalyzed by iridium(I) complexes
    Ishiyama, T
    Sato, K
    Nishio, Y
    Saiki, T
    Miyaura, N
    CHEMICAL COMMUNICATIONS, 2005, (40) : 5065 - 5067
  • [7] Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent
    Ishiyama, T
    Nobuta, Y
    Hartwig, JF
    Miyaura, N
    CHEMICAL COMMUNICATIONS, 2003, (23) : 2924 - 2925
  • [8] Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand
    Karmel, Caleb
    Rubel, Camille Z.
    Kharitonova, Elena V.
    Hartwig, John F.
    Advanced Materials, 2020, 132 (15) : 6130 - 6137
  • [9] Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand
    Karmel, Caleb
    Rubel, Camille Z.
    Kharitonova, Elena V.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (15) : 6074 - 6081
  • [10] Iridium(I)-catalyzed vinylic C-H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron
    Sasaki, Ikuo
    Doi, Hana
    Hashimoto, Toshiya
    Kikuchi, Takao
    Ito, Hajime
    Ishiyama, Tatsuo
    CHEMICAL COMMUNICATIONS, 2013, 49 (68) : 7546 - 7548
1234