Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
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.
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| Auteurs principaux: | , , , , , |
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| Format: | Digital revista |
| Langue: | English |
| Publié: |
Sociedade Brasileira de Química
2013
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| Accès en ligne: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018 |
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