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

Tae Kyu Nam and Doo Ok Jang*

*Department of Chemistry, Yonsei University, Wonju 26493, Republic of Korea, Email:

T. K. Nam, D. O. Jang, J. Org. Chem., 2018, 83, 7373-7379.

DOI: 10.1021/acs.joc.7b03193

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An environmentally benign, tin-free radical "on water" addition of alkyl iodides to the C=N bond of hydrazones in the presence of diphenylsilane and triethylborane afforded the corresponding addition products in good yields. The developed protocol can be applied to the synthesis of 3-substituted isoindolinone derivatives.

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Key Words

hydrazones, diphenylsilane

ID: J42-Y2018