Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity
The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are prefe...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/2/1763 |
| _version_ | 1819210724413538304 |
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| author | Nuria Aiguabella Elsa M. Arce Carlos del Pozo Xavier Verdaguer Antoni Riera |
| author_facet | Nuria Aiguabella Elsa M. Arce Carlos del Pozo Xavier Verdaguer Antoni Riera |
| author_sort | Nuria Aiguabella |
| collection | DOAJ |
| description | The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene. |
| first_indexed | 2024-12-23T06:15:43Z |
| format | Article |
| id | doaj.art-ea62c19f8bae481b90a490e99decceab |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T06:15:43Z |
| publishDate | 2014-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ea62c19f8bae481b90a490e99decceab2022-12-21T17:57:19ZengMDPI AGMolecules1420-30492014-02-011921763177410.3390/molecules19021763molecules19021763Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the RegioselectivityNuria Aiguabella0Elsa M. Arce1Carlos del Pozo2Xavier Verdaguer3Antoni Riera4Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, SpainInstitute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, SpainDepartment de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, SpainInstitute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, SpainInstitute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, SpainThe scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.http://www.mdpi.com/1420-3049/19/2/1763Pauson-Khand reactioncycloadditionsregioselectivitycyclopentenonestrifluoromethylalkynes |
| spellingShingle | Nuria Aiguabella Elsa M. Arce Carlos del Pozo Xavier Verdaguer Antoni Riera Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity Molecules Pauson-Khand reaction cycloadditions regioselectivity cyclopentenones trifluoromethylalkynes |
| title | Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity |
| title_full | Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity |
| title_fullStr | Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity |
| title_full_unstemmed | Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity |
| title_short | Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity |
| title_sort | pauson khand reaction of internal dissymmetric trifluoromethyl alkynes influence of the alkene on the regioselectivity |
| topic | Pauson-Khand reaction cycloadditions regioselectivity cyclopentenones trifluoromethylalkynes |
| url | http://www.mdpi.com/1420-3049/19/2/1763 |
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