Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation

Masayuki Iwasaki, Sayuri Hayashi, Koji Hirano, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation proceeds at 200-250 °C in a toluene-DMF mixed solvent using microwave heating. Even at such high temperatures, the regio- and stereospecificity of the allyl transfer reaction is still satisfactory. The amount of the palladium catalyst can be reduced to 0.5 or 0.05 mol %.

Original languageEnglish
Pages (from-to)5200-5203
Number of pages4
JournalTetrahedron
Volume63
Issue number24
DOIs
Publication statusPublished - Jun 11 2007
Externally publishedYes

Fingerprint

Allylation
Palladium
Microwaves
Alcohols
Microwave heating
Toluene
Heating
Catalysts
Temperature

Keywords

  • Allylation
  • Carbon-carbon bond cleavage
  • Microwaves
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation. / Iwasaki, Masayuki; Hayashi, Sayuri; Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro.

In: Tetrahedron, Vol. 63, No. 24, 11.06.2007, p. 5200-5203.

Research output: Contribution to journalArticle

Iwasaki, Masayuki ; Hayashi, Sayuri ; Hirano, Koji ; Yorimitsu, Hideki ; Oshima, Koichiro. / Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation. In: Tetrahedron. 2007 ; Vol. 63, No. 24. pp. 5200-5203.
@article{55494df9094145918329d42f81956783,
title = "Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation",
abstract = "The palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation proceeds at 200-250 °C in a toluene-DMF mixed solvent using microwave heating. Even at such high temperatures, the regio- and stereospecificity of the allyl transfer reaction is still satisfactory. The amount of the palladium catalyst can be reduced to 0.5 or 0.05 mol {\%}.",
keywords = "Allylation, Carbon-carbon bond cleavage, Microwaves, Palladium",
author = "Masayuki Iwasaki and Sayuri Hayashi and Koji Hirano and Hideki Yorimitsu and Koichiro Oshima",
year = "2007",
month = "6",
day = "11",
doi = "10.1016/j.tet.2007.03.165",
language = "English",
volume = "63",
pages = "5200--5203",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "24",

}

TY - JOUR

T1 - Microwave-assisted palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation

AU - Iwasaki, Masayuki

AU - Hayashi, Sayuri

AU - Hirano, Koji

AU - Yorimitsu, Hideki

AU - Oshima, Koichiro

PY - 2007/6/11

Y1 - 2007/6/11

N2 - The palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation proceeds at 200-250 °C in a toluene-DMF mixed solvent using microwave heating. Even at such high temperatures, the regio- and stereospecificity of the allyl transfer reaction is still satisfactory. The amount of the palladium catalyst can be reduced to 0.5 or 0.05 mol %.

AB - The palladium-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation proceeds at 200-250 °C in a toluene-DMF mixed solvent using microwave heating. Even at such high temperatures, the regio- and stereospecificity of the allyl transfer reaction is still satisfactory. The amount of the palladium catalyst can be reduced to 0.5 or 0.05 mol %.

KW - Allylation

KW - Carbon-carbon bond cleavage

KW - Microwaves

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=34247872786&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34247872786&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.03.165

DO - 10.1016/j.tet.2007.03.165

M3 - Article

VL - 63

SP - 5200

EP - 5203

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 24

ER -