Reactivity of benzyl radicals: The trapping of primary, secondary and tertiary benzyl radicals with heterocyclic bases

A photochemical benzylation of protonated quinolines was realized by single electron transfer (SET) to the excited state of the quinoline from the aromatic reactant. The benzylated product is formed by cross-coupling between the benzyl radical and the heterocyclic radical when they are in close proximity to one another. This allows the formation of products which are, to the best of our knowledge, unaccessible in other ways and which have now been obtained for the first time.