Iridium(I)-catalyzed vinylic C-H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

被引:25
|
作者
Sasaki, Ikuo [1 ]
Doi, Hana [1 ]
Hashimoto, Toshiya [1 ]
Kikuchi, Takao [1 ]
Ito, Hajime [1 ]
Ishiyama, Tatsuo [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan
关键词
CATALYZED DEHYDROGENATIVE BORYLATION; CROSS-COUPLING REACTION; ROOM-TEMPERATURE REACTIONS; EFFICIENT SYNTHESIS; 1-ALKENYL HALIDES; ALKENES; ARENES; ACTIVATION; FUNCTIONALIZATION; COMPLEXES;
D O I
10.1039/c3cc44149k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ir(I)-catalyzed C-H borylation of 1-cycloalkenecarboxylic derivatives with bis(pinacolato)diboron affords various alkenylboronates with functional groups in excellent yields. This reaction was also used in a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.
引用
收藏
页码:7546 / 7548
页数:3
相关论文
共 50 条
  • [1] 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
  • [2] 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
  • [3] Vinylic C-H Borylation of Cyclic Vinyl Ethers with Bis(pinacolato)diboron Catalyzed by an Iridium(I)-dtbpy Complex
    Kikuchi, Takao
    Takagi, Jun
    Isou, Hironori
    Ishiyama, Tatsuo
    Miyaura, Norio
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (12) : 2082 - 2090
  • [4] 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
  • [5] Palladium-catalyzed benzylic C-H borylation of alkylbenzenes with bis(pinacolato)diboron or pinacolborane
    Ishiyama, T
    Ishida, K
    Takagi, J
    Miyaura, N
    CHEMISTRY LETTERS, 2001, (11) : 1082 - 1083
  • [6] Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes
    Ishiyama, Tatsuo
    Isou, Hironori
    Kikuchi, Takao
    Miyaura, Norio
    CHEMICAL COMMUNICATIONS, 2010, 46 (01) : 159 - 161
  • [7] 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
  • [8] Iridium(I)-Catalyzed C-H Borylation in Air by Using Mechanochemistry
    Pang, Yadong
    Ishiyama, Tatsuo
    Kubota, Koji
    Ito, Hajime
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (18) : 4654 - 4659
  • [9] Iridium-catalyzed C-H borylation of pyridines
    Sadler, Scott A.
    Tajuddin, Hazmi
    Mkhalid, Ibraheem A. I.
    Batsanov, Andrei S.
    Albesa-Jove, David
    Cheung, Man Sing
    Maxwell, Aoife C.
    Shukla, Lena
    Roberts, Bryan
    Blakemore, David C.
    Lin, Zhenyang
    Marder, Todd B.
    Steel, Patrick G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (37) : 7318 - 7327
  • [10] Nucleophilic borylation of benzyl halides with bis(pinacolato)diboron catalyzed by palladium(0) complexes
    Ishiyama, T
    Oohashi, Z
    Ahiko, T
    Miyaura, N
    CHEMISTRY LETTERS, 2002, (08) : 780 - 781