Palladium-Catalyzed Cross-Coupling Reactions of Benzyl Indium Reagents with Aryl Iodides

被引：42
|
作者：
Chupak, Louis S. [1 ]
Wolkowski, Joanna P. [1 ]
Chantigny, Yves A. [1 ]
机构：
[1] Pfizer Inc, Groton Labs, Groton, CT 06340 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期
关键词：
ARYLBORONIC ACIDS; HALIDES; DIARYLMETHANES; ORGANOMETALLICS; ALKYLATION; HETEROARYL; CHLORIDES; PARTNERS; METAL;
D O I：
10.1021/jo802280m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein described is an operationally simple procedure for generating benzyl indium species from readily available benzyl bromides and indium metal followed by in situ palladium-catalyzed coupling with aryl halides. The procedure provides diarylmethanes in modest to excellent yield and tolerates a variety of functional groups in both coupling partners.
引用
收藏
页码：1388 / 1390
页数：3
相关论文
共 50 条
  • [1] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF MESITYLCOPPER WITH ARYL IODIDES
    BUMAGIN, NA
    KALINOVSKII, IO
    BELETSKAYA, IP
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 267 (01) : C1 - C3
  • [2] Palladium-catalyzed cross-coupling reactions of triorganoindium compounds with vinyl and aryl triflates or iodides
    Pérez, I
    Sestelo, JP
    Sarandeses, LA
    [J]. ORGANIC LETTERS, 1999, 1 (08) : 1267 - 1269
  • [3] Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides
    Denmark, SE
    Baird, JD
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 793 - 795
  • [4] Palladium-catalyzed cross-coupling reactions of (2-pyridyl)allyldimethylsilanes with aryl iodides
    Nokami, T
    Tomida, Y
    Kamei, T
    Itami, K
    Yoshida, J
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 729 - 731
  • [5] Palladium-catalyzed cross-coupling of benzyl thioacetates and aryl halides
    Wager, Krista M.
    Daniels, Matthew
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Palladium-Catalyzed Cross-Coupling of Benzyl Thioacetates and Aryl Halides
    Wager, Krista M.
    Daniels, Matthew H.
    [J]. ORGANIC LETTERS, 2011, 13 (15) : 4052 - 4055
  • [7] Palladium-catalyzed cross-coupling of aryl electrophiles with dimethylalkynylaluminum reagents
    Wang, BM
    Bonin, M
    Micouin, L
    [J]. ORGANIC LETTERS, 2004, 6 (20) : 3481 - 3484
  • [8] Palladium-catalyzed cross-coupling reactions of aryl mesylates
    So, Chau Ming
    Kwong, Fuk Yee
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4963 - 4972
  • [9] Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate
    Peng, Cheng
    Cheng, Jiajia
    Wang, Jianbo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) : 8708 - +
  • [10] Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides.
    Minehan, TG
    Lehmann, U
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U397 - U397
12345