Tetrahedron

Regioselective synthesis of substituted 1-indanols, 2, 3-dihydrobenzofurans and 2, 3-dihydroindoles by electrochemical radical cyclization using an arene mediator

N Kurono, E Honda, F Komatsu, K Orito, M Tokuda

Index: Kurono, Nobuhito; Honda, Eiichi; Komatsu, Fumikazu; Orito, Kazuhiko; Tokuda, Masao Tetrahedron, 2004 , vol. 60, # 8 p. 1791 - 1801

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Citation Number: 42

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.