A
new methodology of oxidative-dearomatization of planar phenols is described. An economic, viable one-pot metal free protocol for direct conversion of naphthols to α-ketols is reported. Naphthols were found to undergo facile unprecedented oxidative dearomatization with regioselective | |
| hydroxylation with phenyl selenyl Bromide in open air conditions. Quaternary stereocenters were developed along with formation of sterically demanding α- and γ-ketols with high yields. Functional group tolerance like esters is revealed. A through study of the stereoelectronic demands of the unusual oxy-Selenium reactive intermediate involved in dearomatization of 1- and 2-naphthols is studied. 4-hydroxy cyclohexadieneone and cyclohexadieneone aryl ethers were generated form dialkyl-phenols under similar reaction condition providing a direct evidence of the mechanical postulate. The first instance of phenoxy-Selenium interaction leading to facile dearomatization of arenes is highlighted in this manuscript. | |
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