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

Tae Kyu Nam; Doo Ok Jang

doi:10.1021/acs.joc.7b03193

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

Tae Kyu Nam, Doo Ok Jang

Chemistry and Medical Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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 language	English
Pages (from-to)	7373-7379
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	83
Issue number	14
DOIs	https://doi.org/10.1021/acs.joc.7b03193
Publication status	Published - 2018 Jul 20

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2016R1D1A3B03932348).

Publisher Copyright:
© 2018 American Chemical Society.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.7b03193

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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.",

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note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2016R1D1A3B03932348). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Nam, Tae Kyu

AU - Jang, Doo Ok

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2016R1D1A3B03932348). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/7/20

Y1 - 2018/7/20

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AB - 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.

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

Abstract

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