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

Abstract

Treatment of beta-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 beta-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.

• Authors: Yoichiro Kuninobu, Mitsumi Nishi, Salprima Yudha S, Kazuhiko Takai
• Journal: Organic letters (Org Lett) Vol. 10 Issue 14 Pg. 3009-11 (Jul 17 2008) ISSN: 1523-7060 [Print] United States
• PMID: 18549235 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkynes
• Benzene Derivatives
• Ketones
• Manganese

Topics

• Alkynes (chemistry)
• Benzene Derivatives (chemical synthesis, chemistry)
• Catalysis
• Cyclization
• Ketones (chemical synthesis, chemistry)
• Manganese (chemistry)
• Molecular Structure
• Stereoisomerism