Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers
Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers
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DOI：
10.1055/s-2007-983737
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发表时间：
2007-07-03
影响因子：
2.6
通讯作者：
Iwasawa, Nobuharu
中科院分区：
文献类型：
--
作者：
Kusama, Hiroyuki;Funami, Hideaki;Iwasawa, Nobuharu
以PtCl_2为催化剂，邻乙炔基苯甲酸酯或硫代苯甲酸酯与乙烯基醚反应，合成了1-酰基-4-烷氧基萘或1-酰基-4-烷硫基萘。用PtCl处理邻炔基苯甲酸酯衍生物，生成含铂（II）的羰基叶立德作为关键反应中间体，这些物种与乙烯基醚反应，以良好的产率得到取代萘。通过对邻乙炔基苯甲酸酯和[PtCl 2（H2 C = CH 2）]（2）的混合物的NMR分析证实了含铂羰基叶立德的存在。此外，有人认为，萘衍生物的生成是通过叶立德物种与乙烯基醚的[3+2]环加成，然后通过生成的铂-卡宾中间体的1，2-烷基迁移。
A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the PtCl2-catalyzed reaction of o-ethynylbenzoates or benzothioates with vinyl ethers. Treatment of o-alkynylbenzoate derivatives with PtCl, generated the platinum(II)-containing carbonyl ylides as a key reactive intermediate and these species reacted with vinyl ethers to give substituted naphthalenes in good yields. The presence of the platinum-containing carbonyl ylide was confirmed by NMR analyses of the mixture of o-ethynylbenzoate and [PtCl2(H2C=CH2)](2). Furthermore, it was suggested that the naphthalene derivatives were produced by [3+2] cycloaddition of the ylide species with vinyl ethers, followed by 1,2-alkyl migration of the generated platinum-carbene intermediates.