PALLADIUM CATALYZED STEREOSELECTIVE HYDRODEHALOGENATION OF ALKENYL HALIDES WITH TRIBUTYLTIN HYDRIDE

被引:19
|
作者
TANIGUCHI, M [1 ]
TAKEYAMA, Y [1 ]
FUGAMI, K [1 ]
OSHIMA, K [1 ]
UTIMOTO, K [1 ]
机构
[1] KYOTO UNIV, FAC ENGN, DEPT IND CHEM, SAKYO KU, KYOTO 606, JAPAN
关键词
D O I
10.1246/bcsj.64.2593
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reduction of alkenyl halides with tributyltin hydride in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium has been studied. Alkenyl iodides reacted easily with tributyltin hydride at 25-degrees-C to give the corresponding hydrocarbons stereoselectively. However, the reaction of alkenyl bromides were sluggish at 25-degrees-C and needed heating at 75-degrees-C to complete.
引用
收藏
页码:2593 / 2595
页数:3
相关论文
共 50 条
  • [31] Stereoselective synthesis of α-disubstituted cyclopentanones by palladium-catalyzed rearrangement of allenylcyclobutanols with aryl halides
    Yoshida, M
    Sugimoto, K
    Ihara, M
    TETRAHEDRON, 2002, 58 (39) : 7839 - 7846
  • [32] PALLADIUM-CATALYZED REGIOSELECTIVE AND STEREOSELECTIVE CYCLIZED COUPLING OF LITHIUM ALKYNOATES WITH ALLYL HALIDES
    YANAGIHARA, N
    LAMBERT, C
    IRITANI, K
    UTIMOTO, K
    NOZAKI, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2753 - 2754
  • [33] Palladium-Catalyzed Cross-Coupling Reactions with Fluorinated Substrates: Mechanistic Insights into the Undesired Hydrodehalogenation of Aryl Halides
    Orbach, Meital
    Choudhury, Joyanta
    Lahav, Michal
    Zenkina, Olena V.
    Diskin-Posner, Yael
    Leitus, Gregory
    Iron, Mark A.
    van der Boom, Milko E.
    ORGANOMETALLICS, 2012, 31 (04) : 1271 - 1274
  • [34] Facile Synthesis of Steroidal Primary Amides via Palladium-Catalyzed Aminocarbonylation of Steroidal Alkenyl Halides
    Balogh, Janos
    Maho, Sandor
    Hada, Viktor
    Kollar, Laszlo
    Skoda-Foeldes, Rita
    SYNTHESIS-STUTTGART, 2008, (19): : 3040 - 3042
  • [35] Stereoselective synthesis of Z alkenyl halides via Julia olefination
    Lebrun, ME
    Le Marquand, P
    Berthelette, C
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 2009 - 2013
  • [36] Palladium catalyzed carbonylations of alkenyl halides with formic acid to get corresponding α,β-unsaturated carboxylic acids and esters
    Bartal, Brigitta
    Mikle, Gabor
    Kollar, Laszlo
    Pongracz, Peter
    MOLECULAR CATALYSIS, 2019, 467 : 143 - 149
  • [37] The stereoselective synthesis of alkenyl-β-lactams by palladium-catalyzed [2+2] carbonylative cycloaddition
    Troisi, L
    De Vitis, L
    Granito, C
    Epifani, E
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (06) : 1357 - 1362
  • [38] SYNTHESIS OF ENOL ESTERS AND ENOL LACTONES VIA PALLADIUM-CATALYZED CARBONYLATION OF ARYL AND ALKENYL HALIDES
    SHIMOYAMA, I
    ZHANG, YT
    WU, GZ
    NEGISHI, E
    TETRAHEDRON LETTERS, 1990, 31 (20) : 2841 - 2844
  • [39] A one-pot, stereoselective synthesis of 1,3-and 1,4-dienyl sulfones by hydrostannylation-Stille tandem reaction of tributyltin hydride with acetylenic sulfones and alkenyl or allylic halides
    Cai, Mingzhong
    Chen, Guiqin
    Hao, Wenyan
    SYNTHESIS-STUTTGART, 2007, 8 (08): : 1197 - 1203
  • [40] Stereoselective Preparation and Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Sulfoximines
    Yasui, Kosuke
    Tomishima, Yuichiro
    Miura, Tomoya
    Yamazaki, Ken
    Hirano, Koji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (11)