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Palladium-Catalyzed Arylation of the THP Derivative of (Z)-2-Butene-1,4-diol with Arenediazonium Salts and the Synthesis of β-Aryl-γ-butyrolactones

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, 973-977.

DOI: 10.1055/s-0028-1087959 (free Supporting Information)



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Abstract

The reaction of arenediazonium tetrafluoroborates with THP-protected (Z)-2-butene-1,4-diol in the presence of Pd(OAc)2 in MeOH at 35˚C gives 4-aryl-2-methoxytetrahydrofurans in good yields. The reaction tolerates various functional groups including ester, keto, cyano, nitro, chloro, and bromo functionalities as well as ortho substituents. Oxidation with MCPBA gives γ-aryl-β-butyrolactone derivatives.

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Key Words

arenediazonium salts, palladium, Mizoroki-Heck Reaction, tetrahydrofurans, lactols, allylic alcohols


ID: J60-Y2009-1030