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Ligand‐Free Silver(I)‐Catalyzed Intramolecular Friedel–Crafts Alkylation of Arenes with Allylic Alcohols
Author(s) -
Bandini Marco,
Eichholzer Astrid,
Kotrusz Peter,
Tragni Michele,
Troisi Stefano,
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.200800628
Subject(s) - chemistry , friedel–crafts reaction , intramolecular force , trifluoromethanesulfonate , regioselectivity , tsuji–trost reaction , electrophile , alkylation , ligand (biochemistry) , allylic rearrangement , catalysis , tetrahydroisoquinoline , medicinal chemistry , organic chemistry , biochemistry , receptor
The silver‐catalyzed direct activation of allylic alcohols as electrophilic partners for intramolecular Friedel–Crafts alkylation of arenes is described. Use of silver triflate (AgOTf; 10 mol%) enabled functionalized 1‐vinyl‐1,2,3,4‐tetrahydronaphthalenes and a 4‐vinyl‐1,2,3,4‐tetrahydroisoquinoline to be isolated in good yields with high levels of regiochemistry, under a ligand‐free regime.