Radical On Water Addition to the C=N Bond of Hydrazones: A Synthesis of Isoindolinone Derivatives

A radical on water addition to the C=N bond of hydrazones has been described. Hydrazone, diphenylsilane, alkyl iodide, and triethylborane afforded the corresponding addition products on water in good yields. A significant solvent effect was observed from the water. The developed protocol can be applied to the synthesis of 3-substituted isoindolinone derivatives. Moreover, the process offers environmentally benign tin-free radical reaction conditions.