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 journalArticle

6 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 languageEnglish
Pages (from-to)2177-2179
Number of pages3
JournalSynlett
Issue number13
DOIs
Publication statusPublished - Aug 2009
Externally publishedYes

Fingerprint

Bearings (structural)
Cyclobutanes
Palladium
Alcohols
Bromides
Catalysis
cyclopropane

Keywords

  • Allylation
  • Cleavage reactions
  • Homoallyl alcohols
  • Methylenecyclobutanes
  • Palladium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of (2-arylethylidene)cyclobutanes by palladium-catalyzed reactions of aryl halides with homoallyl alcohols bearing a trimethylene group at the allylic position. / Iwasaki, Masayuki; Yorimitsu, Hideki; Oshima, Koichiro.

In: Synlett, No. 13, 08.2009, p. 2177-2179.

Research output: Contribution to journalArticle

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