The Diels-Alder reaction of para-benzoquinones and simple dienes under catalysis with FeCl3 on Aerosil® silica

The Diels-Alder reaction of para-benzoquinones and simple dienes under catalysis with FeCl3 on Aerosil® silica

Donatoni, Maria C.; Junior, Gilmar A. B.; Santos, Alcindo A. Dos; Oliveira, Kleber T. de; Brocksom, Timothy J.

Abstract:

The Diels-Alder reactions of para-benzoquinones and simple dienes produce cycloadducts which serve as important intermediates for the synthesis of bioactive terpenes. These cycloadditions are usually conducted in organic solvents (such as MeOH and CH2Cl2), for several days, or with Lewis acid catalysis in CH2Cl2. The usual Lewis acid catalysts are very efficient, but require anhydrous and oxygen-free conditions. Thus, there is ample scope for improved methodologies for the efficient execution of the Diels-Alder reaction. We have now developed a mild solvent-free protocol for the promotion of these Diels-Alder reactions, catalysed by a mixture of FeCl3 on Aerosil® silica (AS®).

The Diels-Alder reactions of para-benzoquinones and simple dienes produce cycloadducts which serve as important intermediates for the synthesis of bioactive terpenes. These cycloadditions are usually conducted in organic solvents (such as MeOH and CH2Cl2), for several days, or with Lewis acid catalysis in CH2Cl2. The usual Lewis acid catalysts are very efficient, but require anhydrous and oxygen-free conditions. Thus, there is ample scope for improved methodologies for the efficient execution of the Diels-Alder reaction. We have now developed a mild solvent-free protocol for the promotion of these Diels-Alder reactions, catalysed by a mixture of FeCl3 on Aerosil® silica (AS®).

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013913152849

Referências bibliográficas

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• [7] Brocksom, U.; Brocksom, T. J. J. Braz. Chem. Soc. 2008, 19,
• [8] 1484-1489.

Como citar:

Donatoni, Maria C.; Junior, Gilmar A. B.; Santos, Alcindo A. Dos; Oliveira, Kleber T. de; Brocksom, Timothy J.; "The Diels-Alder reaction of para-benzoquinones and simple dienes under catalysis with FeCl3 on Aerosil® silica", p-232-232. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013913152849