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

11 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

Access to Document

10.1021/acs.joc.7b03193

Cite this

@article{107b0fec0a2b442ea3dbd609f1abf2c8,

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

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.",

author = "Nam, {Tae Kyu} and Jang, {Doo Ok}",

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.",

year = "2018",

month = jul,

day = "20",

doi = "10.1021/acs.joc.7b03193",

language = "English",

volume = "83",

pages = "7373--7379",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Radical "on Water" Addition to the C=N Bond of Hydrazones

T2 - A Synthesis of Isoindolinone Derivatives

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

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85048807614&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85048807614&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b03193

DO - 10.1021/acs.joc.7b03193

M3 - Article

C2 - 29498284

AN - SCOPUS:85048807614

VL - 83

SP - 7373

EP - 7379

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 14

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this