Gold-catalyzed consecutive [1,2] alkyl migration-oxygen transfer reaction of 2-alkynyl-1-tetralones

Ching Siew Chan, Toshiharu Araki, Itaru Nakamura, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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 (Ph3P)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.

Original languageEnglish
Pages (from-to)216-218
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number2
DOIs
Publication statusPublished - 2009 Jan 14

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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