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Indium-catalyzed 2-alkenylation of 1,3-dicarbonyl compounds with unactivated alkynes.

Authors
  • Endo, Kohei
  • Hatakeyama, Takuji
  • Nakamura, Masaharu
  • Nakamura, Eiichi
Type
Published Article
Journal
Journal of the American Chemical Society
Publication Date
Apr 25, 2007
Volume
129
Issue
16
Pages
5264–5271
Identifiers
PMID: 17388598
Source
Medline
License
Unknown

Abstract

1,3-Dicarbonyl compounds add to unactivated alkynes in the presence of a catalytic amount of indium(III) trifluoromethanesulfonate in high to excellent yield to give 2-alkenylated 1,3-dicarbonyl compounds with exclusive regioselectivity as to the position of C-C bond formation on the acetylene moiety. In most of the cases, the reaction requires less than 1-mol % loading of the catalyst and does not require solvent. The reaction tolerates a wide variety of functional groups including ester, ether, allylic halide, furan, thiophene, and protected amine. Experimental and theoretical studies suggested that the reaction proceeds via a concerted carbometalation reaction of an indium(III) enolate with the acetylene, where indium-acetylene interaction is important.

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