期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 360, 期 5, 页码 852-858出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701312
关键词
Naphthoquinone(s); Metal-free; Oxidation; NBS; Vicinal tricarbonyls; Chemoselective
资金
- National Research Foundation of Korea grants - Korea Government (MSIP) [MRC 2017R1A5A2015541]
- Basic Science Research Program [2017R1D1A1B03]
- International Science and Business Belt Program through the Ministry of Science, ICT and Future Planning [2017K000490]
A metal-free, one-pot synthesis of 1,2-naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3-dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents.
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