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.
Visible Light Photocatalytic Transformation of α,β-Unsaturated-N-Tosylhydrazones: a Novel Route to Allylic Sulfones
PARISOTTO, STEFANO;CANEPA, Carlo;DIANA, Eliano;PELLEGRINO, FRANCESCO;PRIOLA, EMANUELE;PRANDI, Cristina;MAURINO, Valter;DEAGOSTINO, Annamaria
2017-01-01
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.
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