Palladium(0)-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides

被引：60
|
作者：
Molander, Gary A. [1 ]
Fumagalli, Tiziano [1 ]
机构：
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 15期
关键词：
D O I：
10.1021/jo0608366
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Efficient palladium(0)-catalyzed Suzuki-Miyaura cross-couplings are described. The reactions involving potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides can generally be carried out using <= 2 mol % of palladium catalyst and 3 equiv of base in toluene/H2O. When stereodefined alkenyl bromides are employed, the resulting styrene derivatives are accessed stereospecifically. A variety of functional groups are tolerated in both coupling partners.
引用
收藏
页码：5743 / 5747
页数：5
相关论文
共 50 条
  • [1] Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates
    Molander, GA
    Biolatto, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4302 - 4314
  • [2] Palladium-catalyzed Suzuki-Miyaura reactions of potassium aryl- and heteroaryltrifluoroborates with aryl- and heteroaryl triflates
    Molander, GA
    Petrillo, DE
    Landzberg, NR
    Rohanna, JC
    Biolatto, B
    [J]. SYNLETT, 2005, (11) : 1763 - 1766
  • [3] Scope of the Suzuki-Miyaura Cross-Coupling Reactions of Potassium Heteroaryltrifluoroborates
    Molander, Gary A.
    Canturk, Belgin
    Kennedy, Lauren E.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 973 - 980
  • [4] Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides
    Molander, GA
    Felix, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 3950 - 3956
  • [5] Chemoselective Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of (Diborylmethyl)silanes with Alkenyl Bromides
    Kim, Junghoon
    Lee, Eunsung
    Cho, Seung Hwan
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (09) : 1664 - 1667
  • [6] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
    Molander, Gary A.
    Shin, Inji
    Jean-Gerard, Ludivine
    [J]. ORGANIC LETTERS, 2010, 12 (19) : 4384 - 4387
  • [7] Suzuki-Miyaura cross-coupling reaction of aryl bromides catalyzed by palladium(II) pyridoxal hydrazone complexes
    Pandiarajan, Devaraj
    Ramesh, Rengan
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 708 : 18 - 24
  • [8] Palladium(II) thiosemicarbazone-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl halides
    Pandiarajan, Devaraj
    Ramesh, Rengan
    Liu, Yu
    Suresh, Rajamanickam
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2013, 33 : 33 - 37
  • [9] Suzuki-miyaura cross-coupling reactions of potassium alkenyltrifluoroborates
    Molander, GA
    Bernardi, CR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24): : 8424 - 8429
  • [10] Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
    Molander, Gary A.
    Brown, Adam R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9681 - 9686
12345