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Palladium-catalyzed arylation of enoates with iodobenzene: stereoselective synthesis of trisubstituted olefins
| Content Provider | Scientific Electronic Library Online (SciELO) |
|---|---|
| Author | Fernandes, Talita de A. Vaz, Boniek G. Silva, Alcides J. M. da Esteves, Pierre M. Eberlin, Marcos N. Costa, Paulo R. R. |
| Abstract | 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. |
| Related Links | http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532013000300018&lng=en&nrm=iso http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000300018&lng=en&nrm=iso |
| Starting Page | 500 |
| Ending Page | 506 |
| Page Count | 7 |
| File Format | |
| ISSN | 01035053 |
| DOI | 10.5935/0103-5053.20130067 |
| Journal | Journal of the Brazilian Chemical Society |
| Issue Number | 3 |
| Volume Number | 24 |
| Language | English |
| Publisher | Sociedade Brasileira de Química |
| Publisher Date | 2013-03-01 |
| Publisher Institution | Universidade Federal do Rio de Janeiro Centro de Ciências da Saúde Laboratório de Química Bioorgânica (LQB) Universidade Estadual de Campinas Instituto de Química Laboratório ThoMSon de Espectrometria de Massas Universidade Federal do Rio de Janeiro Instituto de Química Interlab |
| Publisher Place | Brazil |
| Access Restriction | Open |
| Subject Keyword | Heck reaction Enoates Palladium catalysis Mass spectrometry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry |
