LiCl-Mediated Preparation of Functionalized Benzylic Indium(III) Halides and Highly Chemoselective Palladium-Catalyzed Cross-Coupling in a Protic Cosolvent

被引：78
作者：
Chen, Yi-Hung [1 ]
Sun, Mai [1 ]
Knochel, Paul [1 ]
机构：
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 12期
基金：
欧洲研究理事会;
关键词：
biaryls; cross-coupling; organoindium reagents; palladium; REAGENTS; ARYL; ORGANOMETALLICS; COMPLEXES; LIGANDS; ACCESS; ALLYL;
D O I：
10.1002/anie.200805588
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Sensitive functional groups such as COR, CHO, or CH2OH can be present in benzylic indium reagents prepared by the direct insertion of indium in the presence of LiCl. These reagents undergo palladium-catalyzed cross-coupling reactions in the presence of a protic cosolvent after activation with iPrMgCl·LiCl (see scheme). Remarkable chemoselectivities are achieved by using various electrophiles containing NH or OH groups. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：2236 / 2239
页数：4
相关论文
共 59 条
  • [51] Biaryl phosphane ligands in palladium-catalyzed amination
    Surry, David S.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) : 6338 - 6361
  • [52] Suzuki A, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P123, DOI 10.1002/3527606548.ch3
  • [53] Triethylborane-mediated hydrogallation and hydroindation: Novel access to organogalliums and organoindiums
    Takami, K
    Mikami, S
    Yorimitsu, H
    Shinokubo, H
    Oshima, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) : 6627 - 6631
  • [54] Trans-hydrometalation of alkynes by a combination of InCl3 and DIBAL-H:: One-pot access to functionalized (Z)-alkenes
    Takami, K
    Yorimitsu, H
    Oshima, K
    [J]. ORGANIC LETTERS, 2002, 4 (17) : 2993 - 2995
  • [55] Palladium-catalyzed cross-coupling reaction of organoindiums with aryl halides in aqueous media
    Takami, K
    Yorimitsu, H
    Shinokubo, H
    Matsubara, S
    Oshima, K
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 1997 - 1999
  • [56] A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
    Walker, SD
    Barder, TE
    Martinelli, JR
    Buchwald, SL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (14) : 1871 - 1876
  • [57] WALKER SD, 2004, ANGEW CHEM, V116, P1907
  • [58] Wong C.-H., 2003, CARBOHYDRATE BASED D, VFirst
  • [59] Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions
    Yang, Xiaoyin
    Don, Xi
    Muellen, Klaus
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (04) : 759 - 766
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