Ching Siew Chan, T. Araki, I. Nakamura
Jan 14, 2009
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Gold-catalyzed isomerization of 2-alkynyl-1-tetralones afforded the corresponding 2-naphthylmethyl ketones in good to high yields. For example, the reaction of 2-{4-(methoxyphenyl)methyl}-2-(phenylethynyl)-3,4-dihydronaphthalen-1( 2H )-one and 2-benzyl-2-(phenylethynyl)-3,4-dihydronaphthalen-1( 2H )-one in the presence of 5 mol % of (Ph 3 P)AuCl and 5 mol % of AgOTf in THF at 50 °C gave 2-{1-(4-methoxyphenylmethyl)naphthalen-2-yl}-1-(4-methoxyphenyl)ethanone and 2-(1-benzylnaphthalen-2-yl)-1-phenylethanone in 85% and 96% yields, respectively. The present reaction proceeds through [1,2] alkyl migration followed by oxygen transfer.