An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane

被引:158
作者
Billingsley, Kelvin L. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/jo800727s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. This system allows for the conversion of aryl and heteroaryl iodides, bromides, and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed.
引用
收藏
页码:5589 / 5591
页数:3
相关论文
共 15 条
  • [1] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
    Baudoin, O
    Guénard, D
    Guéritte, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9268 - 9271
  • [2] Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies
    Billingsley, Kelvin L.
    Barder, Timothy E.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) : 5359 - 5363
  • [3] Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis
    Broutin, PE
    Cerna, I
    Campaniello, M
    Leroux, F
    Colobert, F
    [J]. ORGANIC LETTERS, 2004, 6 (24) : 4419 - 4422
  • [4] Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system
    Fürstner, A
    Seidel, G
    [J]. ORGANIC LETTERS, 2002, 4 (04) : 541 - 543
  • [5] One pot biaryl synthesis via in situ boronate formation
    Giroux, A
    Han, YX
    Prasit, P
    [J]. TETRAHEDRON LETTERS, 1997, 38 (22) : 3841 - 3844
  • [6] Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548.ch1
  • [7] Metal-catalyzed reactions of diborons for synthesis of organoboron compounds
    Ishiyama, T
    Miyaura, N
    [J]. CHEMICAL RECORD, 2004, 3 (05) : 271 - 280
  • [8] Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes
    Ishiyama, T
    Ishida, K
    Miyaura, N
    [J]. TETRAHEDRON, 2001, 57 (49) : 9813 - 9816
  • [9] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates
    Ishiyama, T
    Itoh, Y
    Kitano, T
    Miyaura, N
    [J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3447 - 3450
  • [10] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
    Kotha, S
    Lahiri, K
    Kashinath, D
    [J]. TETRAHEDRON, 2002, 58 (48) : 9633 - 9695