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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Photochemical benzylic radical arylation promoted by supported Pd nanostructures
Teresa A Gawargy1, Paolo Costa1, Anabel E Lanterna1
1Department of Chemistry and Biomolecular Sciences and Centre for Advanced Materials Research (CAMaR), University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada. anabel.lanterna@icloud.com jscaiano@uottawa.ca.
Abstract:
We report a novel way to promote photochemical benzylic radical arylations using Pd nanostructures. Traditional benzylic radical reaction pathways are challenged by the presence of metal centres that provoke unprecedented regioselectivity towards more synthetically relevant C(sp3)-C(sp2) couplings. This new C-H activation pathway is rationalised by means of a pseudo-persistent radical effect facilitated by metal centres. We show the mechanistic and computational aspects of the heterogeneous photocatalytic processes that are the root of this drastic change in reactivity.
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