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
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1991年 / 64卷 / 08期
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
  • [11] Titanium-Catalyzed Hydrodehalogenation of Alkyl Halides
    Han, Bo
    Ren, Chunping
    Wu, Lipeng
    ORGANOMETALLICS, 2023, 42 (12) : 1248 - 1253
  • [12] Synthesis of Dienes by Palladium-Catalyzed Couplings of Tosylhydrazones with Aryl and Alkenyl Halides
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Aznar, Fernando
    Valdes, Carlos
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3235 - 3240
  • [13] STEREOSELECTIVE REDUCTION OF GLYCOSYL HALIDES BY TRIBUTYLTIN DEUTERIDE
    PRALY, JP
    TETRAHEDRON LETTERS, 1983, 24 (30) : 3075 - 3078
  • [14] Palladium-Catalyzed Carbonylation of Aryl, Alkenyl, and Allyl Halides with Phenyl Formate
    Ueda, Tsuyoshi
    Konishi, Hideyuki
    Manabe, Kei
    ORGANIC LETTERS, 2012, 14 (12) : 3100 - 3103
  • [15] Stereoselective Synthesis of (E)-(Trisubstituted alkenyl)borinic Esters: Stereochemistry Reversed by Ligand in the Palladium-Catalyzed Reaction of Alkynylborates with Aryl Halides
    Ishida, Naoki
    Shimamoto, Yasuhiro
    Murakami, Masahiro
    ORGANIC LETTERS, 2009, 11 (23) : 5434 - 5437
  • [16] PALLADIUM-CATALYZED REACTION OF TRIBUTYLTIN HYDRIDE WITH ACYL CHLORIDES - A SELECTIVE ROUTE TO ALDEHYDES
    GUIBE, F
    FOUR, P
    RIVIERE, H
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (10) : 432 - 433
  • [17] PALLADIUM-CATALYZED HYDRODEHALOGENATION OF HALOAROMATIC COMPOUNDS
    PANDEY, PN
    PURKAYASTHA, ML
    SYNTHESIS-STUTTGART, 1982, (10): : 876 - 878
  • [18] Stereoselective dehalogenation of (Z)-1-halo-1-alkenyldialkylborane with tributyltin hydride: The behavior of tributyltin hydride as a hydride donor
    Hoshi, M
    Takahata, K
    Arase, A
    TETRAHEDRON LETTERS, 1997, 38 (03) : 453 - 456
  • [19] Palladium-catalyzed hydrodehalogenation of aryl halides using paraformaldehyde as the hydride source: high-throughput screening by paper-based colorimetric iodide sensor
    Pyo, Ayoung
    Kim, Sudeok
    Kumar, Manian Rajesh
    Byeun, Aleum
    Eom, Min Sik
    Han, Min Su
    Lee, Sunwoo
    TETRAHEDRON LETTERS, 2013, 54 (38) : 5207 - 5210
  • [20] Stereospecific palladium-catalyzed borylation reaction of 1-alkenyl halides with diispropylaminoborane
    Euzénat, L
    Horhant, D
    Brielles, C
    Alcaraz, G
    Vaultier, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (11) : 2721 - 2724
12345