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

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.