酯作为 Friedel-Crafts 反应中的酰化试剂：三溴化铟催化使用二甲基氯硅烷对芳烃的酰化。

Esters as acylating reagent in a Friedel-Crafts reaction: indium tribromide catalyzed acylation of arenes using dimethylchlorosilane.

机构信息

Department of Applied Chemistry and Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

出版信息

J Org Chem. 2008 Dec 5;73(23):9465-8. doi: 10.1021/jo801914x.

DOI:10.1021/jo801914x

PMID:19007136

Abstract

The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me(2) is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis of the indanone intermediate 11 of salviasperanol from ester 10.

摘要

已通过二甲基氯硅烷和 10mol%三溴化铟实现了芳基与酯的 Friedel-Crafts 酰化反应。关键中间体 RCOOSi(Cl)Me(2)由烷氧基酯生成，同时释放出相应的烷烃。烷氧基酯部分的适用范围很广：叔丁基、苄基、烯丙基和异丙基酯都能成功进行反应。此外，我们还成功地从酯 10 直接合成了蛇床酚的中间产物 11-二氢-1H-茚酮。