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Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes

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We report a direct single-electron oxidation of methylenecyclopropanes (MCPs) for the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives by merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N·3HF (1.0… Click to show full abstract

We report a direct single-electron oxidation of methylenecyclopropanes (MCPs) for the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives by merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N·3HF (1.0 equiv.), the fluorination of MCPs can be realized in the presence of 9-mesityl-10-methylacridinium perchlorate and Co(dmgH)2PyCl, affording fluorinated 4-aryl-1,2-dihydronaphthalene derivatives in moderate yields. In MeCN/HFIP (7 : 3), 4-aryl-1,2-dihydronaphthalene derivatives were obtained in good yields through a MHAT process under similar conditions.

Keywords: single electron; dihydronaphthalene derivatives; visible light; electron oxidation; aryl dihydronaphthalene

Journal Title: Organic chemistry frontiers
Year Published: 2020

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