SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

Kohei Sekine, Yuta Sadamitsu, Tohru Yamada

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

C-C bond-forming carboxylation and cyclization of trimethyl(2-methylenebut-3-yn-1-yl)silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.

Original languageEnglish
Pages (from-to)5706-5709
Number of pages4
JournalOrganic Letters
Volume17
Issue number22
DOIs
Publication statusPublished - Nov 20 2015
Externally publishedYes

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carboxylation
Carboxylation
Silanes
Cyclization
alkynes
silanes
cascades
Alkynes
Derivatives
dioxides
alkenes
crystallography
carbon dioxide
isomers
selectivity
X Ray Crystallography
silver
Alkenes
Silver
catalysts

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives. / Sekine, Kohei; Sadamitsu, Yuta; Yamada, Tohru.

In: Organic Letters, Vol. 17, No. 22, 20.11.2015, p. 5706-5709.

Research output: Contribution to journalArticle

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