Platinum(II)-catalyzed reaction of 2-alkynylbenzoates or benzothioates with vinyl ethers: a concise method for synthesis of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalene derivatives

Hiroyuki Kusama; Hideaki Funami; Jun Takaya; Nobuharu Iwasawa

doi:10.1021/ol0364024

Platinum(II)-catalyzed reaction of 2-alkynylbenzoates or benzothioates with vinyl ethers: a concise method for synthesis of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalene derivatives

Org Lett. 2004 Feb 19;6(4):605-8. doi: 10.1021/ol0364024.

Authors

Hiroyuki Kusama¹, Hideaki Funami, Jun Takaya, Nobuharu Iwasawa

Affiliation

¹ Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

PMID: 14961634
DOI: 10.1021/ol0364024

Abstract

[reaction: see text] A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the reaction of o-ethynylbenzoates or benzothioates with vinyl ethers, in the presence of a catalytic amount of PtCl(2). It is proposed that the reaction proceeds through [3 + 2]-cycloaddition of the platinum-containing carbonyl ylides followed by 1,2-alkyl migration.