Diethylzinc: A Chain-Transfer Agent in Intermolecular Radical Additions. A Parallel with Triethylborane

Abstract

In the presence of oxygen, diethylzinc can be used to promote radical additions to CN bond containing radical acceptors and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to CC bond containing radical acceptors such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.