Tandem carbon-carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4'-disubstituted 1,1'-binaphthols

Chemical Communications : Chem Comm
Kentaro OkumaKosei Shioj


An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoylacetones in refluxing acetonitrile to give 4-aryl-2-naphthols and 3-aryl-1-naphthols.


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