Stereospecific preparation of (Z)-α-fluorostilbenes via a kinetically controlled palladium-catalyzed cross-coupling reaction of high E/Z ratio 1-bromo-1-fluorostyrenes and aryl stannanes

被引：25
|
作者：
Xu, JJ [1 ]
Burton, DJ [1 ]
机构：
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 15期
基金：
美国国家科学基金会;
关键词：
fluorostilbenes; palladium-catalyzed cross-coupling; stereospecific; isomerization; bromofluoroalkenes; kinetic separation;
D O I：
10.1016/S0040-4039(02)00357-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
High E/Z ratios were obtained for 1-bromo-1-fluorostyrenes by isomerization from the original E/Z ratios of approximately 1:1. The palladium-catalyzed cross-coupling reaction of high E/Z ratio 1-bromo-1-fluorostyrenes with aryl stannanes gives (Z)-alpha-fluorostilbenes stereospecifically in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2877 / 2879
页数：3
相关论文
共 50 条
  • [31] A DIRECT SYNTHESIS OF 6-PYRIDINYL-2(1H)-QUINOLINONES VIA PALLADIUM-CATALYZED CROSS-COUPLING REACTION
    BELL, AS
    ROBERTS, DA
    RUDDOCK, KS
    [J]. SYNTHESIS-STUTTGART, 1987, (09): : 843 - 844
  • [32] CONDENSED HETEROAROMATIC RING-SYSTEMS .18. PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ARYL BROMIDES WITH (Z)-1-ETHOXY-2-TRIBUTYLSTANNYLETHENE AND ITS UTILIZATION FOR CONSTRUCTION OF CONDENSED HETEROAROMATICS
    SAKAMOTO, T
    KONDO, Y
    YASUHARA, A
    YAMANAKA, H
    [J]. TETRAHEDRON, 1991, 47 (10-11) : 1877 - 1886
  • [33] Synthesis of Acyl Alkenylindium Reagents and Their Application in the Synthesis of (Z)-α,β-Unsaturated Ketones via Palladium-Catalyzed Cross-Coupling Reaction (vol 17, pg 3934, 2015)
    Park, Youngchul
    Min, Jiae
    Eom, Dahan
    Lee, Phil Ho
    [J]. ORGANIC LETTERS, 2015, 17 (18) : 4649 - 4649
  • [34] Stereospecific preparation of symmetrical (1Z,3Z) 2,3-difluoro-1,4-disubstituted-buta-1,3-dienes by the coupling reaction between bis(tributyltin) and high E/Z 1-bromo-1-fluoroalkenes
    Xu, JJ
    Burton, DJ
    [J]. TETRAHEDRON LETTERS, 2002, 43 (25) : 4565 - 4567
  • [35] Synthesis of 1,1-Disubstituted Indenes via Palladium-Catalyzed Cross-Coupling of ortho-Alkenyl Bromobenzenes and a-Aryl-a- diazoesters
    Feng, Xiao-Jiao
    Fu, Jian-Guo
    Zhao, Qian
    Lu, Yu-Han
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    [J]. SYNTHESIS-STUTTGART, 2023, 55 (12): : 1922 - 1928
  • [36] The first enantiospecific synthesis of (-)-koumidine via the intramolecular palladium-catalyzed enolate driven cross coupling reaction.: The stereospecific introduction of the 19-(Z) ethylidene side chain
    Cao, H
    Yu, JM
    Wearing, XYZ
    Zhang, CC
    Liu, XX
    Deschamps, J
    Cook, JM
    [J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 8013 - 8017
  • [37] STEREOSELECTIVE SYNTHESIS OF ALLYLIC BORONATES VIA PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF KNOCHEL (DIALKOXYBORYL)METHYLZINC REAGENTS WITH 1-HALO-1-ALKENES
    WATANABE, T
    MIYAURA, N
    SUZUKI, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 444 (1-2) : C1 - C3
  • [38] Synthesis of 1-alkenylboronic esters via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides and triflates
    Takahashi, K
    Takagi, J
    Ishiyama, T
    Miyaura, N
    [J]. CHEMISTRY LETTERS, 2000, (02) : 126 - 127
  • [39] A facile stereoselective synthesis of difunctionalized 1,3-dienes containing silicon and tin via palladium-catalyzed cross-coupling reaction
    Cai, MZ
    Zhou, Z
    Wang, PP
    [J]. SYNTHESIS-STUTTGART, 2006, (05): : 789 - 792
  • [40] STEREOSELECTIVE SYNTHESIS OF CONJUGATED DIENONES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORONATES WITH 3-HALO-2-ALKEN-1-ONES
    SATOH, N
    ISHIYAMA, T
    MIYAURA, N
    SUZUKI, A
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) : 3471 - 3473
12345