Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position

Masayuki Iwasaki; Hideki Yorimitsu; Koichiro Oshima

doi:10.1055/s-0029-1217703

Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position

Masayuki Iwasaki, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-arylethylidene) cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retroallylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.

Original language	English
Pages (from-to)	2177-2179
Number of pages	3
Journal	Synlett
Issue number	13
DOIs	https://doi.org/10.1055/s-0029-1217703
Publication status	Published - Aug 2009
Externally published	Yes

Keywords

Allylation
Cleavage reactions
Homoallyl alcohols
Methylenecyclobutanes
Palladium

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position",

abstract = "Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-arylethylidene) cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retroallylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.",

keywords = "Allylation, Cleavage reactions, Homoallyl alcohols, Methylenecyclobutanes, Palladium",

author = "Masayuki Iwasaki and Hideki Yorimitsu and Koichiro Oshima",

year = "2009",

month = aug,

doi = "10.1055/s-0029-1217703",

language = "English",

pages = "2177--2179",

journal = "Synlett",

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T1 - Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position

AU - Iwasaki, Masayuki

AU - Yorimitsu, Hideki

AU - Oshima, Koichiro

PY - 2009/8

Y1 - 2009/8

N2 - Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-arylethylidene) cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retroallylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.

AB - Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-arylethylidene) cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retroallylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.

KW - Allylation

KW - Cleavage reactions

KW - Homoallyl alcohols

KW - Methylenecyclobutanes

KW - Palladium

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JF - Synlett

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ER -

Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position

Abstract

Keywords

ASJC Scopus subject areas

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