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

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

doi:10.1016/j.tet.2007.03.165

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 journal › Article › peer-review

28 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 language	English
Pages (from-to)	5200-5203
Number of pages	4
Journal	Tetrahedron
Volume	63
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2007.03.165
Publication status	Published - Jun 11 2007
Externally published	Yes

Keywords

Allylation
Carbon-carbon bond cleavage
Microwaves
Palladium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.03.165

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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",

note = "Funding Information: This work is supported by Grants-in-Aid for Scientific Research and COE Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. K.H. acknowledges JSPS for financial support. ",

year = "2007",

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doi = "10.1016/j.tet.2007.03.165",

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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

N1 - Funding Information: This work is supported by Grants-in-Aid for Scientific Research and COE Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. K.H. acknowledges JSPS for financial support.

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

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DO - 10.1016/j.tet.2007.03.165

M3 - Article

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SN - 0040-4020

VL - 63

SP - 5200

EP - 5203

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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