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
  • [31] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES
    STILLE, JK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06): : 508 - 523
  • [32] Palladium-catalyzed cross-coupling reactions of carboxylic anhydrides with organozinc reagents
    Wang, DH
    Zhang, ZG
    [J]. ORGANIC LETTERS, 2003, 5 (24) : 4645 - 4648
  • [33] Palladium-catalyzed cross-coupling of aryl esters
    Dardir, Amira
    Melvin, Patrick
    Hazari, Nilay
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [34] PALLADIUM-CATALYZED CYCLIZATION AND CROSS-COUPLING OF ACETYLENIC ARYL TRIFLATES WITH ORGANOTIN REAGENTS
    LUO, FT
    WANG, RT
    [J]. TETRAHEDRON LETTERS, 1991, 32 (52) : 7703 - 7706
  • [35] A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents
    He, Xiao-Yun
    [J]. MONATSHEFTE FUR CHEMIE, 2021, 152 (07): : 823 - 832
  • [36] A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents
    Xiao-Yun He
    [J]. Monatshefte für Chemie - Chemical Monthly, 2021, 152 : 823 - 832
  • [37] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF VINYL AND ARYL TRIFLATES WITH TETRAARYLBORATES
    CIATTINI, PG
    MORERA, E
    ORTAR, G
    [J]. TETRAHEDRON LETTERS, 1992, 33 (33) : 4815 - 4818
  • [38] Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols
    Denmark, SE
    Ober, MH
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1703 - 1714
  • [39] PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING OF ORGANOBORANES WITH ARYL IODIDES OR BENZYL HALIDES IN THE PRESENCE OF BIS(ACETYLACETONATO)ZINC(II)
    WAKITA, Y
    YASUNAGA, T
    AKITA, M
    KOJIMA, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (02) : C17 - C20
  • [40] PREPARATION OF ETHYL ARYLPROPIOLATES FROM ARYL IODIDES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTION
    SAKAMOTO, T
    SHIGA, F
    YASUHARA, A
    UCHIYAMA, D
    KONDO, Y
    YAMANAKA, H
    [J]. SYNTHESIS-STUTTGART, 1992, (08): : 746 - 748