Journal of the American Chemical Society, Vol.142, No.5, 2396-2403, 2020
Radical Reactions in Cavitands Unveil the Effects of Affinity on Dynamic Supramolecular Systems
Radical reduction of alkyl halides and aerobic oxidation of alkyl aromatics are reported using water-soluble container compounds (1 and 2). The reductions involve alpha,omega-dihalides (4-8 and 10) with radical initiators in cavitand hosts with varied binding affinities. Product distributions lead to general guidelines for the use of dynamic supramolecular systems with fast reactions. The binding of guest substrates in the hosts must show high affinities (K-a > 10(3) M-1) to ensure that the reactions take place under confinement in the containers.