1,2-Halogen migration in haloallenyl ketones: Regiodivergent synthesis of halofurans

Anna W. Sromek, Marina Rubina, Vladimir Gevorgyan

Research output: Contribution to journalArticle

303 Citations (Scopus)

Abstract

Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans.

Original languageEnglish (US)
Pages (from-to)10500-10501
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number30
DOIs
StatePublished - Aug 3 2005
Externally publishedYes

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Bromine
Halogens
Ketones
Catalysts
Chlorine
Iodine
Hydrogen

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

1,2-Halogen migration in haloallenyl ketones : Regiodivergent synthesis of halofurans. / Sromek, Anna W.; Rubina, Marina; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 127, No. 30, 03.08.2005, p. 10500-10501.

Research output: Contribution to journalArticle

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