Esters as acylating reagent in a Friedel-Crafts reaction: indium tribromide catalyzed acylation of arenes using dimethylchlorosilane.
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.
Nishimoto
Yoshihiro
Y
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.
Babu
Srinivasarao Arulananda
SA
Yasuda
Makoto
M
Baba
Akio
A
D000107:Acetylation; D000473:Alkanes / Q000737:chemistry; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D017606:Chlorine Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D012821:Silanes / Q000737:chemistry*
D000473:Alkanes; D001965:Bromides; D017606:Chlorine Compounds; D004952:Esters; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D012821:Silanes; D007204:Indium