Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones.
The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds at room temperature, under p-TsOH catalysis, affords substituted polycyclic aromatic indene derivatives through a domino reaction involving the formation of a cationic allenylium intermediate. This species can undergo a series of competitive intramolecular cascade reactions, leading to a conjugated inden-2-one. This simple method allows the efficient synthesis of substituted indenes and inden-2-ones, in two steps, from aromatic ketones.
Centro de Quı́mica-Vila Real, Universidade de Trás-os-Montes e Alto Douro , 5000-801 Vila Real, Portugal.
Céu M
CM
Sousa
Jerome
J
Berthet
Stephanie
S
Delbaere
Paulo J
PJ
Coelho
D000143:Acids / Q000737:chemistry*; D002072:Butylene Glycols / Q000737:chemistry*; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000143:Acids; D002072:Butylene Glycols; D002412:Cations; D007192:Indenes; D007659:Ketones