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

Yoshihiro Nishimoto; Srinivasarao Arulananda Babu; Makoto Yasuda; Akio Baba

doi:10.1021/jo801914x

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

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

Authors

Yoshihiro Nishimoto¹, Srinivasarao Arulananda Babu, Makoto Yasuda, Akio Baba

Affiliation

¹ 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.

PMID: 19007136
DOI: 10.1021/jo801914x

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylation
Alkanes / chemistry
Bromides / chemistry*
Catalysis
Chemistry, Organic / methods*
Chlorine Compounds / chemistry*
Esters / chemistry
Hydrocarbons, Brominated / chemistry
Hydrocarbons, Chlorinated / chemistry
Indium / chemistry*
Magnetic Resonance Spectroscopy / methods
Models, Chemical
Silanes / chemistry*

Substances

Alkanes
Bromides
Chlorine Compounds
Esters
Hydrocarbons, Brominated
Hydrocarbons, Chlorinated
Silanes
Indium