期刊
SYNLETT
卷 28, 期 13, 页码 1554-1557出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588155
关键词
oxidation; nitroxyl radical; primary alcohols; aldehydes; chemoselectivity
资金
- MEXT
- JSPS KAKENHI [16K080162]
- Platform Project for Supporting in Drug Discovery and Life Science Research from AMED
- JSPS [16J04480]
- Grants-in-Aid for Scientific Research [16J04480] Funding Source: KAKEN
The 2-azaadamantane-N-oxyl (AZADO)- and 9-azanoradamantane-N-oxyl (nor-AZADO)-catalyzed selective oxidation of primary alcohols to the corresponding aldehydes is described. The use of tert-butyl nitrite as the co-catalyst enables efficient aerobic oxidation in MeCN instead of previously reported AcOH; this is important for the selectivity of the reaction. The addition of a solution of saturated aqueous NaHCO3 after the completion of the reaction was effective to suppress the overoxidation of the product to the corresponding carboxylic acid during the workup.
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