Iron(III)-Catalyzed Intramolecular Friedel–Crafts Alkylation of Electron-Deficient Arenes with π-Activated Alcohols

✍ Scribed by Marco Bandini; Michele Tragni; Achille Umani-Ronchi

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 171 KB
• Volume: 351
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200900441

✦ Synopsis

Abstract

“Deficient” but “efficient”, the first example of a catalytic Friedel–Crafts alkylation of arenes, carrying electron‐withdrawing groups, with alcohols is reported. The optimized iron(III) chloride (97%) catalyzed allylation, benzylation and propargylation procedures open an access to a range of tetrahydronaphthalenes, tetrahydroisoquinolines and tetrahydrobenzo[d]azepines featuring tertiary benzylic stereocenters in excellent yields (up to 92%) and short reaction times.