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Communication | Regular issue | Vol 38, No. 7, 1994, pp.1487-1490
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6744
Regioselective Prenylation of Phenols by Palladium Catalyst: Syntheses of Prenylphenols and Chromans

Masao Tsukayama,* Makoto Kikuchi, and Yasuhiko Kawamura

*Department of Chemical Science and Technology, Faculty of Engineering, University of Tokushima, Minamijosanjima-cho, Tokushima 770-8506, Japan


The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2). Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4). Dehydration of alkylphenols (3f-h) gave chromans (7).