Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes
Using heterogeneous photocatalysis, the radical addition of tertiary amines with electron deficient alkenes can be performed in high yields (up to 98%) and high facial diastereoselectivity. The photochemical induced electron transfer process initiates the radical chain reaction and inorganic semicon...
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| Format: | Article |
| Language: | English |
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Wiley
2003-01-01
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| Series: | International Journal of Photoenergy |
| Online Access: | http://dx.doi.org/10.1155/S1110662X03000308 |
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| _version_ | 1832551505357438976 |
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| author | Siniša Marinković Norbert Hoffmann |
| author_facet | Siniša Marinković Norbert Hoffmann |
| author_sort | Siniša Marinković |
| collection | DOAJ |
| description | Using heterogeneous photocatalysis, the radical addition of tertiary amines with electron deficient
alkenes can be performed in high yields (up to 98%) and high facial diastereoselectivity. The photochemical
induced electron transfer process initiates the radical chain reaction and inorganic semiconductors
like TiO2 and ZnS were used. According to the proposed mechanism, the reaction takes place at the surface
of the semiconductor and the termination step results from an interfacial electron transfer from the conduction
band to the oxoallyl radical intermediate. Frequently, semiconductors are used for the mineralisation
of organic compounds in wastewater. However, in this case, they are used in organic synthesis. The process
can be performed in a convenient way and is particularly interesting from the ecological and economical
point of view. No previous functionalization of the tertiary amines is necessary for C − C bond formation.
Further on, the amines are used both as reactant and as solvent. The excess is recycled by distillation and the
inexpensive sensitiser can be easily removed by filtration. In this way, products of high interest for organic
synthesis are obtained by a diastereoselective radical reaction. |
| format | Article |
| id | doaj-art-fc92b4e7952e48b9a5a6ef2863931e57 |
| institution | Kabale University |
| issn | 1110-662X |
| language | English |
| publishDate | 2003-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | International Journal of Photoenergy |
| spelling | doaj-art-fc92b4e7952e48b9a5a6ef2863931e572025-02-03T06:01:18ZengWileyInternational Journal of Photoenergy1110-662X2003-01-015317518210.1155/S1110662X03000308Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenesSiniša Marinković0Norbert Hoffmann1Equipe Photochimie, Laboratoire de Réactions Sélectives et Applications, UMR 6519, CNRS et Université de Reims Champagne-Ardenne, UFR Sciences BP 1039, Reims, Cedex 02 F-51687, FranceEquipe Photochimie, Laboratoire de Réactions Sélectives et Applications, UMR 6519, CNRS et Université de Reims Champagne-Ardenne, UFR Sciences BP 1039, Reims, Cedex 02 F-51687, FranceUsing heterogeneous photocatalysis, the radical addition of tertiary amines with electron deficient alkenes can be performed in high yields (up to 98%) and high facial diastereoselectivity. The photochemical induced electron transfer process initiates the radical chain reaction and inorganic semiconductors like TiO2 and ZnS were used. According to the proposed mechanism, the reaction takes place at the surface of the semiconductor and the termination step results from an interfacial electron transfer from the conduction band to the oxoallyl radical intermediate. Frequently, semiconductors are used for the mineralisation of organic compounds in wastewater. However, in this case, they are used in organic synthesis. The process can be performed in a convenient way and is particularly interesting from the ecological and economical point of view. No previous functionalization of the tertiary amines is necessary for C − C bond formation. Further on, the amines are used both as reactant and as solvent. The excess is recycled by distillation and the inexpensive sensitiser can be easily removed by filtration. In this way, products of high interest for organic synthesis are obtained by a diastereoselective radical reaction.http://dx.doi.org/10.1155/S1110662X03000308 |
| spellingShingle | Siniša Marinković Norbert Hoffmann Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes International Journal of Photoenergy |
| title | Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| title_full | Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| title_fullStr | Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| title_full_unstemmed | Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| title_short | Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| title_sort | semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes |
| url | http://dx.doi.org/10.1155/S1110662X03000308 |
| work_keys_str_mv | AT sinisamarinkovic semiconductorsassensitisersfortheradicaladditionoftertiaryaminestoelectrondeficientalkenes AT norberthoffmann semiconductorsassensitisersfortheradicaladditionoftertiaryaminestoelectrondeficientalkenes |