Photoinduced C-C bond cleavage for the synthesis of 2,4-disubstituted-1-naphthols from indenone derivatives and sulfoxonium ylide.

Org Biomol Chem

Program on Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Center of Excellence on Environmental Health and Toxicology, CHE, Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.

Published: July 2022

The synthesis of 2,4-disubstituted-1-naphthols has been developed employing photomediated C-C bond cleavage (UV-LED 390 nm) of cyclopropane fused-indanones generated from the reaction between indenones and trimethylsulfoxonium chloride under basic conditions at room temperature. Seventeen substrates were examined in this study. The results showed that indenone precursors containing aryl substituents could smoothly provide the desired products in up to 81% yield.

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http://dx.doi.org/10.1039/d2ob00958gDOI Listing

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