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

Prapas Khorphueng; Jumreang Tummatorn; Wacharakorn Patumanon; Charnsak Thongsornkleeb; Sukit Chonradeenitchakul; Somsak Ruchirawat

doi:10.1039/D2OB00958G

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

Prapas Khorphueng,^a Jumreang Tummatorn,

*^bc Wacharakorn Patumanon,^c Charnsak Thongsornkleeb,

^bc Sukit Chonradeenitchakul^b and Somsak Ruchirawat^bc

Author affiliations

* Corresponding authors

^a Department of Chemistry, Faculty of Science, Mahanakorn University of Technology, 140 Chueam Samphan Rd, Krathum Rai, Nong Chok, Bangkok, Thailand

^b 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

^c Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
E-mail: jumreang@cri.or.th

Abstract

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 in situ 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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Article information

DOI: https://doi.org/10.1039/D2OB00958G
Article type: Paper
Submitted: 19 May 2022
Accepted: 15 Jun 2022
First published: 15 Jun 2022

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Org. Biomol. Chem., 2022,20, 5520-5524

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

P. Khorphueng, J. Tummatorn, W. Patumanon, C. Thongsornkleeb, S. Chonradeenitchakul and S. Ruchirawat, Org. Biomol. Chem., 2022, 20, 5520 DOI: 10.1039/D2OB00958G

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Organic & Biomolecular Chemistry

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

Abstract

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

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