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

Bandini Marco | Zendy; Tragni Michele | Zendy; UmaniRonchi Achille | Zendy

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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.

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