Synthesis of Prenylarenes and Related (Multisubstituted Allyl)arenes from Aryl Halides and Homoallyl Alcohols via Palladium-Catalyzed Retro-Allylation

被引:17
|
作者
Iwasaki, Masayuki [1 ]
Yorimitsu, Hideki [1 ]
Shima, Koichiro [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
关键词
CROSS-COUPLING REACTIONS; ORGANIC-SYNTHESIS; PHOTOSUBSTITUTION; DICYANOBENZENES;
D O I
10.1246/bcsj.82.249
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reactions of aryl halides with 2,3,3-trimethyl-4-penten-2-ol in the presence of a palladium catalyst result in prenyl transfer from the alcohol to aryl halides via retro-allylation, yielding prenylarenes. Other multisubstituted allyl groups such as the 2,3-dimethyl-2-butenyl group are introduced to aromatic rings.
引用
收藏
页码:249 / 253
页数:5
相关论文
共 50 条
  • [1] Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation
    Iwasaki, Masayuki
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    TETRAHEDRON, 2007, 63 (24) : 5200 - 5203
  • [2] Palladium-catalyzed Heck cyclization/allylation with homoallyl alcohols via retro-allylation
    Zhou, Ping-Xin
    Yang, Xiaozhe
    Du, Xueyan
    Zhao, Shujie
    Wang, Han
    Li, Xinguang
    Liu, Ning
    Tan, Xinqiang
    Ren, Feng
    Liang, Yong-Min
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (15): : 4097 - 4103
  • [3] Palladium-catalyzed stereo- and regiospecific allylation of aryl halides with homoallyl alcohols via retro-allylation:: Selective generation and use of σ-allylpalladium
    Hayashi, S
    Hirano, K
    Yorimitsu, H
    Oshima, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) : 2210 - 2211
  • [4] Palladium-catalyzed stereo- and regiospecific allylation of aryl halides with homoallyl alcohols via retro-allylation: Selective generation and use of σ-allylpalladium
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    Journal of the American Chemical Society, 2006, 128 (07): : 2210 - 2211
  • [5] Rhodium-catalyzed allyl transfer from homoallyl alcohols to acrylate esters via retro-allylation
    Jang, Minsul
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    TETRAHEDRON LETTERS, 2007, 48 (23) : 4003 - 4005
  • [6] Rhodium-catalyzed allyl transfer from homoallyl alcohols to aldehydes via retro-allylation followed by isomerization into ketones
    Takada, Yuko
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    ORGANIC LETTERS, 2006, 8 (12) : 2515 - 2517
  • [7] Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes
    Sumida, Yuto
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    ORGANIC LETTERS, 2008, 10 (08) : 1629 - 1632
  • [8] Pd(OAc)2/P(cC6H11)3-Catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation
    Iwasaki, Masayuki
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (14) : 4463 - 4469
  • [9] Pd(OAc)2/P(cC6H11) 3-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation
    Iwasaki, Masayuki
    Hayashi, Sayuri
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    Journal of the American Chemical Society, 2007, 129 (14): : 4463 - 4469
  • [10] Synthesis of Epoxides by Palladium-Catalyzed Reactions of Tertiary Allyl Alcohols with Aryl or Alkenyl Halides
    Hayashi, Sayuri
    Yorimitsu, Hideki
    Oshima, Koichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) : 2052 - +