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EnglishIn this paper, the first example of a visible light driven transformation of α,β-unsaturated sulfonylhydrazones to allylic sulfones is described. The reaction is carried out in very mild conditions affording allylic sulfones by generation of highly delocalized radicals, crucial in promoting nitrogen loss instead of the commonly observed intramolecular hydroamination. Moreover, the mechanism has been investigated demonstrating the generation of a vinyl radical intermediate.
| Titolo: | Visible Light Photocatalytic Transformation of α,β-Unsaturated-N-Tosylhydrazones: a Novel Route to Allylic Sulfones |
| Autori Riconosciuti: | |
| Autori: | Parisotto, Stefano; Garreffa, Gabriele; Canepa, Carlo; Diana, Eliano; Pellegrino, Francesco; Priola, Emanuele; Prandi, Cristina; Maurino, Valter; Deagostino, Annamaria |
| Data di pubblicazione: | 2017 |
| Abstract: | In this paper, the first example of a visible light driven transformation of α,β-unsaturated sulfonylhydrazones to allylic sulfones is described. The reaction is carried out in very mild conditions affording allylic sulfones by generation of highly delocalized radicals, crucial in promoting nitrogen loss instead of the commonly observed intramolecular hydroamination. Moreover, the mechanism has been investigated demonstrating the generation of a vinyl radical intermediate. |
| Volume: | 1 |
| Fascicolo: | 2 |
| Pagina iniziale: | 56 |
| Pagina finale: | 59 |
| Digital Object Identifier (DOI): | 10.1002/cptc.201600037 |
| URL: | http://onlinelibrary.wiley.com/doi/10.1002/cptc.201600037/full |
| Parole Chiave: | Visible light, photocatalysis, α,β-unsaturated tosylhydrazones, allyl sulfones, hydrazonyl radicals. |
| Rivista: | CHEMPHOTOCHEM |
| Appare nelle tipologie: | 03A-Articolo su Rivista |
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