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Iron(III)‐Catalyzed Intramolecular Friedel–Crafts Alkylation of Electron‐Deficient Arenes with π‐Activated Alcohols
Author(s) -
Bandini Marco,
Tragni Michele,
UmaniRonchi Achille
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900441
Subject(s) - chemistry , friedel–crafts reaction , stereocenter , alkylation , catalysis , intramolecular force , medicinal chemistry , chloride , organic chemistry , iron(iii) chloride , enantioselective synthesis
“ 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.