Palladium-catalyzed cross-coupling reactions of allyl, phenyl, alkenyl, and alkynyl germatranes with aryl iodides

被引:55
|
作者
Faller, JW [1 ]
Kultyshev, RG [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/om020578c
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The potential of using organogermatranes in palladium-catalyzed cross-coupling with aryl iodides has been investigated. We have found that organogermatranes are less reactive in this analogue of Stille coupling than trialkylorganostannanes; nevertheless activation by fluoride promotes the reaction. The hypervalent germanium species produced from the germatranes provide a more efficient and more easily handled reagent than trialkoxygermanium. analogues.
引用
收藏
页码:5911 / 5918
页数:8
相关论文
共 50 条
  • [31] Palladium-catalyzed cross-coupling reactions with aryl nonaflates:: A practical alternative to aryl triflates
    Rottländer, M
    Knochel, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01): : 203 - 208
  • [32] MECHANISTIC ASPECTS OF AQUEOUS PALLADIUM-CATALYZED ARYL-ARYL CROSS-COUPLING REACTIONS
    WALLOW, TI
    NOVAK, BM
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 247 - INOR
  • [33] PALLADIUM-CATALYZED CROSS-COUPLING REACTION - DIRECT ALLYLATION OF ARYL BROMIDES WITH ALLYL ACETATE
    YOKOYAMA, Y
    ITO, S
    TAKAHASHI, Y
    MURAKAMI, Y
    [J]. TETRAHEDRON LETTERS, 1985, 26 (52) : 6457 - 6460
  • [34] Palladium-catalyzed cross-coupling reaction of allyl acetates with pinacol aryl- and vinylboronates
    Ortar, G
    [J]. TETRAHEDRON LETTERS, 2003, 44 (23) : 4311 - 4314
  • [35] Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols
    Rosa, David
    Nikolaev, Andrei
    Nithiy, Nisha
    Orellana, Arturo
    [J]. SYNLETT, 2015, 26 (04) : 441 - 448
  • [36] Palladium-catalyzed cross-coupling of cyclopropylboronic acids with alkenyl triflates
    Yao, ML
    Deng, MZ
    [J]. TETRAHEDRON LETTERS, 2000, 41 (47) : 9083 - 9087
  • [37] MECHANISM OF PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS
    JUTAND, A
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 121 - ORGN
  • [38] Xantphos as an efficient ligand for palladium-catalyzed cross-coupling reactions of aryl bromides and triflates with allyl acetates and indium
    Seomoon, Dong
    Lee, Phil Ho
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03): : 1165 - 1168
  • [39] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
    Schmink, Jason R.
    Krska, Shane W.
    Tudge, Matthew T.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [40] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL CHLORIDES WITH ARYLSILATRANES
    Yamamoto, Yutaro
    Baralle, Alexandre
    Godefroy, Anais
    Murakami, Kei
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    [J]. HETEROCYCLES, 2017, 95 (01) : 568 - 574