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

Journal of the Brazilian Chemical Society

Silva, Alcides J. M. da¹  Universidade Estadual de Campinas, Campinas, Brazil¹  Eberlin, Marcos N.¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Vaz, Boniek G.¹  Costa, Paulo R. R.¹  Universidade Federal de Goiás, Goiânia, Brazil¹  Esteves, Pierre M.¹  Fernandes, Talita de A.¹ 

关键词: Heck reaction;    enoates;    palladium catalysis;    mass spectrometry;   

DOI  :  10.5935/0103-5053.20130067

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

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 stereoselectivity observed was rationalized through the classic mechanism of the Heck reaction.

【 授权许可】

Unknown