Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins

Resumo

The Heck reaction between E- and Z-enoates and iodobenzene was studied in the presence of Pd(OAc)2. The stereochemistry in resulting adducts was dependent on the enoate geometry (stereospecific reaction). Best yields were obtained from Z-isomers in acetone using Ag2CO3 as base. The main cationic palladium intermediates possibly involved in the catalytic cycle could be intercepted and characterized by electrospray ionization mass spectrometry (ESI-MS). The

Descrição

Palavras-chave

Heck reaction, Enoates, Palladium catalysis, Mass spectrometry

Citação

FERNANDES, Talita de A. et al. Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins. Journal of the Brazilian Chemical Society, Campinas, v. 24, n. 3, p. 500-506, 2013.