Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates

Lourdes Villar, Joseph P. Bullock, Matheen M. Khan, Arumugam Nagarajan, Roderick W. Bates, Simon G. Bott, Gerardo Zepeda, Francisco Delgado, Joaquin Tamariz

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

10 Citas (Scopus)

Resumen

The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph3P)2PdCl2 also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.

Idioma originalInglés
Páginas (desde-hasta)9-17
Número de páginas9
PublicaciónJournal of Organometallic Chemistry
Volumen517
N.º1-2
DOI
EstadoPublicada - 28 jun. 1996

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