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

Journal of the Brazilian Chemical Society

Talita De A. Fernandes²  Boniek G. Vaz¹  Alcides J. M. Da Silva²  Pierre M. Esteves¹  Marcos N. Eberlin¹  Paulo R. R. Costa² 

[1] ,Universidade Federal do Rio de Janeiro Centro de Ciências da Saúde Laboratório de Química Bioorgânica (LQB)Rio de Janeiro RJ ,Brazil

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

DOI  :  10.5935/0103-5053.20130067

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】

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