Ruthenium-Catalyzed ortho C-H Borylation of Arylphosphines

被引:63
|
作者
Fukuda, Kazuishi [1 ]
Iwasawa, Nobuharu [1 ]
Takaya, Jun [1 ,2 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Sch Sci, Meguro Ku, Tokyo 1528551, Japan
[2] JST, PRESTO, Kawaguchi, Saitama 3320012, Japan
关键词
arenes; borylation; C-H activation; phosphines; ruthenium; TERTIARY PHOSPHINE; ORTHO-ARYLATION; ACTIVATION; CONSTRUCTION; DERIVATIVES; GENERATION; COMPLEXES; ALKENES;
D O I
10.1002/anie.201813278
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Efficient, phosphine-directed ortho C-H borylation of arylphosphine derivatives was achieved using Ru catalysts for the first time. The reaction is applicable to various tertiary arylphosphine and arylphosphinite derivatives to give (o-borylaryl)phosphorus compounds in high yields. This reaction enables easy access to a variety of functionalized phosphine ligands and ambiphilic phosphine boronate compounds, thus realizing a new late-stage modification of phosphorus compounds.
引用
收藏
页码:2850 / 2853
页数:4
相关论文
共 50 条
  • [1] Ruthenium-catalyzed regiospecific borylation of methyl C-H bonds
    Murphy, Jaclyn M.
    Lawrence, Joshua D.
    Kawamura, Kazumori
    Incarvito, Christopher
    Hartwig, John F.
    Journal of the American Chemical Society, 2006, 128 (42): : 13684 - 13685
  • [2] Ruthenium-catalyzed nitrogen-directed ortho C-H borylation of aromatic imines with pinacolborane
    Maeda, Yuna
    Sato, Masaru
    Okada, Shinsuke
    Murata, Miki
    TETRAHEDRON LETTERS, 2018, 59 (26) : 2537 - 2540
  • [3] Ruthenium-catalyzed regiospecific borylation of methyl C-H bonds
    Murphy, Jaclyn M.
    Lawrence, Joshua D.
    Kawamura, Kazumori
    Incarvito, Christopher
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) : 13684 - 13685
  • [4] Ruthenium-catalyzed regio- and site-selective ortho C-H borylation of phenol derivatives
    Homma, Yuki
    Fukuda, Kazuishi
    Iwasawa, Nobuharu
    Takaya, Jun
    CHEMICAL COMMUNICATIONS, 2020, 56 (73) : 10710 - 10713
  • [5] Ruthenium-Catalyzed Functional-Group-Directed C-H Silylation and Borylation
    Murata, Miki
    Maeda, Yuna
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2019, 77 (09) : 876 - 882
  • [6] Ruthenium-NHC complex-catalyzed P(iii)-directed C-H borylation of arylphosphines
    Thongpaen, Jompol
    Manguin, Romane
    Kittikool, Tanakorn
    Camy, Aurele
    Roisnel, Thierry
    Dorcet, Vincent
    Yotphan, Sirilata
    Canac, Yves
    Mauduit, Marc
    Basle, Olivier
    CHEMICAL COMMUNICATIONS, 2022, 58 (86) : 12082 - 12085
  • [7] Ruthenium-catalyzed addition of aromatic imines at the ortho C-H bonds to olefins
    Kakiuchi, F
    Yamauchi, M
    Chatani, N
    Murai, S
    CHEMISTRY LETTERS, 1996, (02) : 111 - 112
  • [8] Ruthenium-catalyzed addition of aromatic esters at the ortho C-H bonds to olefins
    Sonoda, M
    Kakiuchi, F
    Kamatani, A
    Chatani, N
    Murai, S
    CHEMISTRY LETTERS, 1996, (02) : 109 - 110
  • [9] Ruthenium-Catalyzed C-H Selenylations of Benzamides
    Ma, Wenbo
    Weng, Zhengyun
    Fang, Xinyue
    Gu, Linghui
    Song, Yupin
    Ackermann, Lutz
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (01) : 41 - 45
  • [10] Ruthenium-catalyzed C-H activation of thioxanthones
    Wagner, Danny
    Braese, Stefan
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 431 - 435