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
  • [1] [Anonymous], 1967, METHODS ELEMENTO ORG
  • [2] [Anonymous], 1991, COMPREHENSIVE ORGANI
  • [3] ATWOOD JD, 1995, COMPREHENSIVE ORGANO, V8, P303, DOI DOI 10.1016/B978-008046519-7.00074-5
  • [4] Hydroborations catalysed by transition metal complexes
    Beletskaya, I
    Pelter, A
    [J]. TETRAHEDRON, 1997, 53 (14) : 4957 - 5026
  • [5] BORWN HC, 1962, HYDROBORATION
  • [6] Role of the phospholipase C-inositol 1,4,5-trisphosphate pathway in calcium release-activated calcium current and capacitative calcium entry
    Broad, LM
    Braun, FJ
    Lievremont, JP
    Bird, GSJ
    Kurosaki, T
    Putney, JW
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (19) : 15945 - 15952
  • [7] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS
    BURGESS, K
    OHLMEYER, MJ
    [J]. CHEMICAL REVIEWS, 1991, 91 (06) : 1179 - 1191
  • [8] REACTIONS OF 2-PHENYL-4H-1,3,2-BENZODIOXABORIN, A STABLE ORTHO-QUINONE METHIDE PRECURSOR
    CHAMBERS, JD
    CRAWFORD, J
    WILLIAMS, HWR
    DUFRESNE, C
    SCHEIGETZ, J
    BERNSTEIN, MA
    LAU, CK
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (06): : 1717 - 1732
  • [9] New N- and O-arylations with phenylboronic acids and cupric acetate
    Chan, DMT
    Monaco, KL
    Wang, RP
    Winters, MP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
  • [10] Chen HY, 1999, ANGEW CHEM INT EDIT, V38, P3391, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3391::AID-ANIE3391>3.0.CO