Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage

Yoichiro Kuninobu, Hisatsugu Takata, Atsushi Kawata, Kazuhiko Takai

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

(Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

Original languageEnglish
Pages (from-to)3133-3135
Number of pages3
JournalOrganic Letters
Volume10
Issue number14
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

Fingerprint

Rhenium
Acetylene
aromatic compounds
Aromatic compounds
rhenium
cleavage
Esters
Bearings (structural)
Aromatization
acetylene
esters
Carbon Monoxide
synthesis
Derivatives
Catalysts
catalysts
single bond
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage. / Kuninobu, Yoichiro; Takata, Hisatsugu; Kawata, Atsushi; Takai, Kazuhiko.

In: Organic Letters, Vol. 10, No. 14, 01.12.2008, p. 3133-3135.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Takata, Hisatsugu ; Kawata, Atsushi ; Takai, Kazuhiko. / Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage. In: Organic Letters. 2008 ; Vol. 10, No. 14. pp. 3133-3135.
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