Regioselective synthesis of substituted 1-indanols, 2,3-dihydrobenzofurans and 2,3-dihydroindoles by electrochemical radical cyclization using an arene mediator |
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| Authors: | Nobuhito Kurono Eiichi Honda Fumikazu Komatsu Kazuhiko Orito Masao Tokuda |
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| Institution: | Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, kita-ku kita13 Nishi8, Sapporo 060-8628, Japan |
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| Abstract: | Electrochemical reduction of haloarenes carrying 2-(1-hydroxybut-3-enyl), 2-allyloxy or N-allyl-N-methylamino group in the presence of phenanthrene as a mediator generated the corresponding aryl radicals and gave the corresponding 5-exo cyclization products in good yields. Higher regio- and stereoselectivities than those of usual radical cyclization using AIBN-Bu3SnH were achieved. |
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| Keywords: | Electrolysis Radical cyclization 5-exo Cyclization Arene mediator Regioselectivity |
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