Journal
ACS OMEGA
Volume 1, Issue 5, Pages 799-807Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.6b00235
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Funding
- Japan Society for the Promotion of Science (JSPS) [16H04138, 16K14049]
- Nanotechnology Platform Program of Nara Institute of Science and Technology (NAIST)
- Grants-in-Aid for Scientific Research [16H04138, 26410056, 16K14049] Funding Source: KAKEN
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The oxidative coupling of benzylamines proceeds efficiently using salicylic acid derivatives as organo-catalysts under an oxygen atmosphere, affording the corresponding N-benzylidenebenzylamines in high yields. Electron-rich salicylic acid derivatives such as 4,6-dimethoxysalicylic acid and 4,6-dihydroxysalicylic acid exhibit excellent catalytic activities for the oxidative coupling of benzylamines to give the corresponding imines. This amine oxidation can also be applied to the synthesis of nitrogen-containing heterocycles such as benzimidazole derivatives. Furthermore, to recycle the catalyst, silica gel supported with 4.7 wt % of 4,6-dihydroxysalicylic acid is prepared, which acts as a recyclable catalyst, oxidizing benzylamine to imine four times successfully.
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