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 tetr...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-10, Vol.351 (14-15), p.2521-2524
Main Authors: Bandini, Marco, Tragni, Michele, Umani-Ronchi, Achille
Format: Article
Language:English
Subjects:
alcohols
aromatic compounds
electron-deficient compounds
Friedel-Crafts alkylation
iron
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Summary:“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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900441