期刊
CHEMICAL & PHARMACEUTICAL BULLETIN
卷 53, 期 2, 页码 199-206出版社
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.53.199
关键词
1-naphthol; 2,2 '-binapthyl; pi-acceptor; p-benzoquinone; oxidative coupling; arylation
We investigated the reactions of various 1-naphthols (NPOHs; 1) with p-benzoquinones (Qs), such as 1,4-benzoquinone (BQ) and p-chloranil (CA), as pi-electron acceptors. With electron-rich NPOHs la-c, oxidative biaryl coupling and subsequent dehydrogenation reaction took place selectively to give the corresponding 2,2'-binapthyl-1,1'-quinones 3a-c in excellent yield. In the case of electron-deficient NPOHs le, f, two different types of reactions occurred in the presence of SnCl4 and ZrO2 under similar conditions: SnCl4 mediated oxidative dimerization and trimerization of NPOH, while ZrO2 promoted electrophilic arylation of Qs with NPOH. The resulting products 3 would be useful synthetic intermediates for naturally occurring diosindigo B, biramentaceone and violet-quinone.
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