Transition metal-catalyzed borylation of alkanes and arenes via C-H activation

被引:278
作者
Ishiyama, T [1 ]
Miyaura, N [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan
关键词
transition metal complexes; bis(pinacolato)diboron; pinacolborane; hydrocarbon; organoboron compound; C-H borylation;
D O I
10.1016/S0022-328X(03)00176-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Since 1999, direct borylation of hydrocarbons catalyzed by a transition metal complex has been extensively studied by several groups and has become an economical, efficient, elegant, and environmentally benign protocol for the synthesis of a variety of organoboron compounds. Re-, Rh-, Ir- and Pd-catalyzed C-H borylation of alkanes, arenes and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane provide alkyl-, aryl-, heteroaryl- and benzylboron compounds, respectively, In this review, seminal early works and exciting recent developments in the area of direct borylation of hydrocarbons via C-H activation are summarized. (C) 2003 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:3 / 11
页数:9
相关论文
共 93 条
  • [81] Suzuki A, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P49
  • [82] 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
    [J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5649 - 5651
  • [83] Molecular design of artificial molecular and ion recognition systems with allosteric guest responses
    Takeuchi, M
    Ikeda, M
    Sugasaki, A
    Shinkai, S
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) : 865 - 873
  • [84] The use of boron clusters in the rational design of boronated nucleosides for neutron capture therapy of cancer
    Tjarks, W
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 614 : 37 - 47
  • [85] NITROGEN DONORS IN ORGANOMETALLIC CHEMISTRY AND HOMOGENEOUS CATALYSIS
    TOGNI, A
    VENANZI, LM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (05): : 497 - 526
  • [86] Regioselective aromatic borylation in an inert solvent
    Tse, MK
    Cho, JY
    Smith, MR
    [J]. ORGANIC LETTERS, 2001, 3 (18) : 2831 - 2833
  • [87] VAULTIER M, 1995, COMPREHENSIVE ORGANO, V11, P191
  • [88] C-H activation and functionalization of unsaturated hydrocarbons by transition-metal boryl complexes
    Waltz, KM
    Muhoro, CN
    Hartwig, JF
    [J]. ORGANOMETALLICS, 1999, 18 (17) : 3383 - 3393
  • [89] Selective functionalization of alkanes by transition-metal boryl complexes
    Waltz, KM
    Hartwig, JF
    [J]. SCIENCE, 1997, 277 (5323) : 211 - 213
  • [90] Theoretical investigation on functionalization of alkanes by a rhodium complex catalyst
    Wan, XH
    Wang, XJ
    Luo, Y
    Takami, S
    Kubo, M
    Miyamoto, A
    [J]. ORGANOMETALLICS, 2002, 21 (18) : 3703 - 3708