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Article Dans Une Revue Tetrahedron Année : 2022

Selective palladium-catalyzed functionalization of α-methylene butanolides

Résumé

We describe an efficient and selective functionalization of α-methylene-γ-butyrolactone. The two-step sequence involves the preparation of bromomethylene butyrolactone 2 in good yield prior to a palladium-catalyzed coupling process. The latter allowed the installation of aryl, alkenyl, and alkynyl groups under Suzuki-Miyaura, Heck, and Sonogashira cross-coupling conditions. The reaction sequences involving Pd(dppf)Cl2-CsF, Pd(OAc)2-PPh3-Ag2CO3, Pd(PPh4)4-CuI-Et3N as the corresponding catalytic systems allow the preparation of an unprecedented panel of α-unsaturated substituted butyrolactones 4–16 ranging from moderate to excellent yields. In all cases, the E-configuration of the exo-double bond is retained from the starting materials to the targets, regardless of the nature of the substituent introduced.

Domaines

Chimie
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Dates et versions

hal-03830713 , version 1 (26-10-2022)

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Citer

Arbia Talbi, Aïcha Arfaoui, Mohamed Lotfi Efrit, Anne Gaucher, Hédi M'Rabet, et al.. Selective palladium-catalyzed functionalization of α-methylene butanolides. Tetrahedron, 2022, 122, pp.132926. ⟨10.1016/j.tet.2022.132926⟩. ⟨hal-03830713⟩
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