Premium
Iron‐Catalyzed Arene Prenylation
Author(s) -
VillaniGale Alexander J.,
Eichman Chad C.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600531
Subject(s) - chemistry , prenylation , isoprene , friedel–crafts reaction , regioselectivity , catalysis , derivatization , organic chemistry , stereochemistry , combinatorial chemistry , enzyme , polymer , copolymer , high performance liquid chromatography
The syntheses of prenylated arenes and 2,2‐dimethylchromans using a Friedel–Crafts‐type coupling between activated arenes and isoprene is reported. A combination of catalytic amounts of FeCl 3 and AgBF 4 promotes a regioselective prenylation event followed by a cyclization to form a 2,2‐dimethylchroman structure. The method avoids isoprene polymerization and allows the facile late‐stage derivatization of biologically active motifs.