Premium
Visible‐Light‐Driven Photocatalytic Transformation of α,β‐Unsaturated‐ N ‐Tosylhydrazones: A Novel Route to Allylic Sulfones
Author(s) -
Parisotto Stefano,
Garreffa Gabriele,
Canepa Carlo,
Diana Eliano,
Pellegrino Francesco,
Priola Emanuele,
Prandi Cristina,
Maurino Valter,
Deagostino Annamaria
Publication year - 2017
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201600037
Subject(s) - allylic rearrangement , photocatalysis , hydroamination , intramolecular force , delocalized electron , radical , photochemistry , chemistry , organic chemistry , catalysis
The first example of a visible‐light‐driven transformation of α,β‐unsaturated sulfonylhydrazones to allylic sulfones is described. The reaction is carried out under 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.