Arylchlorogermanes/TBAF/"Moist" Toluene: A Promising Combination for Pd-Catalyzed Germyl-Stille Cross-Coupling

被引:25
作者
Zhang, Zun-Ting [1 ]
Pitteloud, Jean-Philippe [1 ]
Cabrera, Laura [1 ]
Liang, Yong [1 ]
Toribio, Myrdich [1 ]
Wnuk, Stanislaw F. [1 ]
机构
[1] Florida Int Univ, Dept Chem & Biochem, Miami, FL 33199 USA
关键词
BIARYL SYNTHESIS; ARYL HALIDES; TETRABUTYLAMMONIUM TRIPHENYLDIFLUOROSILICATE; ALKYNYL GERMATRANES; KINETIC-ANALYSIS; ORGANIC HALIDES; PALLADIUM; TRIS(TRIMETHYLSILYL)GERMANES; REAGENTS; VINYL;
D O I
10.1021/ol9028918
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trichlorophenyl,- dichlorodiphenyl,- and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of TBAF in toluene with addition of the measured amount of water. One chloride ligand on the Ge center allows efficient activation by fluoride to promote transfer of one, two, or three phenyl groups from the organogermane precursors.
引用
收藏
页码:816 / 819
页数:4
相关论文
共 34 条
  • [1] Chen C, 1999, J ORG CHEM, V64, P3476
  • [2] de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
  • [3] Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols
    Denmark, SE
    Ober, MH
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1703 - 1714
  • [4] Fluoride-promoted cross-coupling reactions of alkenylsilanols. Elucidation of the mechanism through spectroscopic and kinetic analysis
    Denmark, SE
    Sweis, RF
    Wehrli, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4865 - 4875
  • [5] Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis
    Denmark, SE
    Sweis, RF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4876 - 4882
  • [6] Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates
    Denmark, SE
    Sweis, RF
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3771 - 3774
  • [7] Cross-coupling of vinylpolysiloxanes with aryl iodides
    Denmark, SE
    Wang, ZG
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 372 - 375
  • [8] Palladium-catalyzed cross-coupling reaction using arylgermanium sesquioxide
    Endo, Mayuko
    Fugami, Keigo
    Enokido, Tatsuki
    Sano, Hiroshi
    Kosugi, Masanori
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (07) : 1025 - 1027
  • [9] Palladium-catalyzed cross-coupling reaction by means of organogermanium trichlorides
    Enokido, T
    Fugami, K
    Endo, M
    Kameyama, M
    Kosugi, M
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1685 - 1688
  • [10] Alkynyl germatranes as alternative reagents for the preparation of biarylethynes
    Faller, JW
    Kultyshev, RG
    Parr, J
    [J]. TETRAHEDRON LETTERS, 2003, 44 (03) : 451 - 453