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

Tae Kyu Nam, Doo Ok Jang

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Abstract

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.

Original languageEnglish
Pages (from-to)7373-7379
Number of pages7
JournalJournal of Organic Chemistry
Volume83
Issue number14
DOIs
Publication statusPublished - 2018 Jul 20

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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