Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes

Yoichiro Kuninobu, Mitsumi Nishi, Salprima S. Yudha, Kazuhiko Takai

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) 5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

Original languageEnglish
Pages (from-to)3009-3011
Number of pages3
JournalOrganic Letters
Volume10
Issue number14
DOIs
Publication statusPublished - 2008

Fingerprint

Alkynes
Manganese
Benzene
acetylene
manganese
esters
Esters
benzene
Cycloaddition
aromatic compounds
Aromatic compounds
Molecular sieves
Cycloaddition Reaction
cycloaddition
absorbents
Carbon Monoxide
Dehydration
dehydration
Derivatives
acetophenone

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes. / Kuninobu, Yoichiro; Nishi, Mitsumi; Yudha, Salprima S.; Takai, Kazuhiko.

In: Organic Letters, Vol. 10, No. 14, 2008, p. 3009-3011.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Nishi, Mitsumi ; Yudha, Salprima S. ; Takai, Kazuhiko. / Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes. In: Organic Letters. 2008 ; Vol. 10, No. 14. pp. 3009-3011.
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