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Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

Sandro Cacchi*, Giancarlo Fabrizi, Antonella Goggiamani, Alessio Sferrazza

*Dipartimento di Chimica e Tecnologie del Farmaco, UniversitÓ degli Studi ‘La Sapienza', P. le A. Moro 5, 00185 Rome, Italy, Email: sandro.cacchiuniroma1.it

S. Cacchi, G. Fabrizi, A. Goggiamani, A. Sferrazza, Synlett, 2009, 1277-1280.

DOI: 10.1055/s-0028-1088132 (free Supporting Information)


Abstract

The mild, palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate in MeOH gives 4-arylbutenolides in good yields through a domino vinylic substitution/cyclization process. The reaction tolerates halogen substituents, nitro, ether, cyano, keto, and ester groups and can be performed as a one-pot process generating the arenediazonium salt in situ.

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Key Words

diazonium salts, Heck reaction, cyclization, butenolides, rubrolides


ID: J60-Y2009-1500