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Selective palladium-catalyzed functionalization of α-methylene butanolides

Talbi, Arbia ; Arfaoui, Aïcha ; Efrit, Mohamed Lotfi ; Gaucher, Anne ; M'Rabet, Hédi ; Prim, Damien

Tetrahedron, 2022-09, Vol.122, p.132926, Article 132926 [Periódico revisado por pares]

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Título:
Selective palladium-catalyzed functionalization of α-methylene butanolides
Autor: Talbi, Arbia ; Arfaoui, Aïcha ; Efrit, Mohamed Lotfi ; Gaucher, Anne ; M'Rabet, Hédi ; Prim, Damien
Assuntos: Butenolide ; Butyrolactone ; Chemical Sciences ; Palladium
É parte de: Tetrahedron, 2022-09, Vol.122, p.132926, Article 132926
Descrição: 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. [Display omitted]
Editor: Elsevier Ltd
Idioma: Inglês

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