4,4,6-trimethyl-1,3,2-dioxaborinane: A practical reagent for palladium-catalyzed borylation of aryl halides

被引:18
|
作者
Murata, Miki [1 ]
Oda, Takeshi [1 ]
Watanabe, Shinji [1 ]
Masuda, Yuzuru [1 ]
机构
[1] Kitami Inst Technol, Dept Mat Sci, Kitami, Hokkaido 0908507, Japan
来源
SYNTHESIS-STUTTGART | 2007年 / 03期
关键词
boron; palladium; catalysis; cross-coupling; aryl halides;
D O I
10.1055/s-2006-958962
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed borylation of aryl iodides with 4,4,6-trimethyl-1,3,2-dioxaborinane is described. The mild reaction conditions employed allow for aryl iodides with a wide variety of functional groups to be tolerated. The products of this borylation were coupled with aryl halides to give biaryls in good yields.
引用
收藏
页码:351 / 354
页数:4
相关论文
共 50 条
  • [21] 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane: a superior 2-carbon building block for vinylboronate Heck couplings
    Lightfoot, AP
    Maw, G
    Thirsk, C
    Twiddle, SJR
    Whiting, A
    TETRAHEDRON LETTERS, 2003, 44 (41) : 7645 - 7648
  • [22] Mechanism of the Palladium-Catalyzed Borylation of Aryl Halides with Pinacolborane
    Lam, King Chung
    Marder, Todd B.
    Lin, Zheyang
    ORGANOMETALLICS, 2010, 29 (07) : 1849 - 1857
  • [23] Synthesis of Aryl Triolborates via Nickel-Catalyzed Borylation of Aryl Halides with 5-(tert-Butyldimethylsiloxymethyl)-5-methyl-1,3,2-dioxaborinane
    Sogabe, Yosuke
    Namikoshi, Takeshi
    Watanabe, Shinji
    Murata, Miki
    SYNTHESIS-STUTTGART, 2012, 44 (08): : 1233 - 1236
  • [24] Conformational analysis of 2,4,5-trimethyl-1,3,2-dioxaborinane individual stereoisomers
    O. Yu. Valiakhmetova
    S. A. Bochkor
    V. V. Kuznetsov
    Russian Journal of General Chemistry, 2009, 79 : 1102 - 1105
  • [25] Conformational analysis of 2,4,5-trimethyl-1,3,2-dioxaborinane individual stereoisomers
    Valiakhmetova, O. Yu.
    Bochkor, S. A.
    Kuznetsov, V. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2009, 79 (06) : 1102 - 1105
  • [26] Reaction of 2-isobutyl-4,4,6-trimethyl-1,3,2-oxazaborinane with acetonitrile
    Kuznetsov, VV
    ZHURNAL ORGANICHESKOI KHIMII, 1997, 33 (01): : 140 - 141
  • [27] NEW SYNTHESES OF 2-IMINOXY-4,4,6-TRIMETHYL-1,3,2-DIOXABORINANES
    SINGH, A
    MEHROTRA, RC
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1974, 4 (06): : 557 - 565
  • [28] 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane: An efficient and selective 2-carbon building block for vinylboronate Suzuki-Miyaura coupling reactions
    Lightfoot, AP
    Twiddle, SJR
    Whiting, A
    SYNLETT, 2005, (03) : 529 - 531
  • [29] An efficient catalyst system for palladium-catalyzed borylation of aryl halides with pinacolborane
    Murata, Miki
    Sambommatsu, Tomoko
    Watanabe, Shinji
    Masuda, Yuzuru
    SYNLETT, 2006, (12) : 1867 - 1870
  • [30] An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane
    Billingsley, Kelvin L.
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5589 - 5591