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

Abstract

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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Citations

Mar 2, 2016·The Journal of Organic Chemistry·Ramagonolla KranthikumarSrivari Chandrasekhar
Apr 12, 2013·Chemistry : a European Journal·Jih Ru Hwu, Sharada P Swain
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li

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