Iridium-Mediated Borylation of Benzylic C-H Bonds by Borohydride

被引:40
作者
Tang, Christina Y. [1 ]
Smith, William [1 ]
Thompson, Amber L. [1 ]
Vidovic, Dragoslav [1 ]
Aldridge, Simon [1 ]
机构
[1] Univ Oxford, Inorgan Chem Lab, S Parks Rd, Oxford OX1 3QR, England
基金
英国工程与自然科学研究理事会;
关键词
boron; borylation; C-H activation; iridium; N-heterocyclic ligands; N-HETEROCYCLIC CARBENE; CATALYZED BORYLATION; COMPLEXES; RHODIUM; ACTIVATION; ARENES; PINACOLBORANE; FUNCTIONALIZATION; INTERMEDIATE; CHEMISTRY;
D O I
10.1002/anie.201006320
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple source: An intramolecular iridium-mediated C-H borylation proceeds through transfer of a BH3 fragment from borohydride to a benzylic carbon center (see scheme; coe=cyclooctene). Simple and inexpensive LiBH 4 is thus utilized as the boron source in C-H to C-B conversion. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1359 / 1362
页数:4
相关论文
共 39 条
  • [1] Hydrophobically directed selective reduction of ketones
    Biscoe, MR
    Breslow, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) : 12718 - 12719
  • [2] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes
    Boller, TM
    Murphy, JM
    Hapke, M
    Ishiyama, T
    Miyaura, N
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14263 - 14278
  • [3] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
    Cho, JY
    Tse, MK
    Holmes, D
    Maleczka, RE
    Smith, MR
    [J]. SCIENCE, 2002, 295 (5553) : 305 - 308
  • [4] Steric and chelate directing effects in aromatic borylation
    Cho, JY
    Iverson, CN
    Smith, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12868 - 12869
  • [5] Getting the sterics just right: a five-coordinate iridium trisboryl complex that reacts with C-H bonds at room temperature
    Chotana, Ghayoor A.
    Vanchura, Britt A., II
    Tse, Man Kin
    Staples, Richard J.
    Maleczka, Robert E., Jr.
    Smith, Milton R., III
    [J]. CHEMICAL COMMUNICATIONS, 2009, (38) : 5731 - 5733
  • [6] Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters
    Coventry, DN
    Batsanov, AS
    Goeta, AE
    Howard, JAK
    Marder, TB
    Perutz, RN
    [J]. CHEMICAL COMMUNICATIONS, 2005, (16) : 2172 - 2174
  • [7] IRIDIUM AND RHODIUM DIHYDRIDE HYDROBORATE COMPLEXES OF TYPE [MH2(BH4)L2]
    EMPSALL, HD
    MENTZER, E
    SHAW, BL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (21) : 861 - 862
  • [8] N-Heterocyclic carbenes.: Part 48.: Rhodium and iridium complexes of N-heterocyclic carbenes:: Structural investigations and their catalytic properties in the borylation reaction
    Frey, Guido D.
    Rentzsch, Christoph F.
    von Preysing, Denise
    Scherg, Tobias
    Muehlhofer, Michael
    Herdtweck, Eberhardt
    Herrmann, Wolfgang A.
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (26) : 5725 - 5738
  • [9] (PENTAMETHYLCYCLOPENTADIENYL)IRIDIUM POLYHYDRIDE COMPLEXES - SYNTHESIS OF INTERMEDIATES IN THE MECHANISM OF FORMATION OF (C5(CH3)5)IRH4 AND THE PREPARATION OF SEVERAL IRIDIUM(V) COMPOUNDS
    GILBERT, TM
    HOLLANDER, FJ
    BERGMAN, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) : 3508 - 3516
  • [10] Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548