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 | |
| Publication status | Published - 2018 Jul 20 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
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Radical "on Water" Addition to the C=N Bond of Hydrazones : A Synthesis of Isoindolinone Derivatives. / Nam, Tae Kyu; Jang, Doo Ok.
In: Journal of Organic Chemistry, Vol. 83, No. 14, 20.07.2018, p. 7373-7379.Research output: Contribution to journal › Article
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
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 -