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Alkylation of Arenes with Benzylic and Propargylic Alcohols – Classical versus Fancy Catalysts
Author(s) -
Liu Jianhui,
Muth Enrico,
Flörke Ulrich,
Henkel Gerald,
Merz Klaus,
Sauvageau Janelle,
Schwake Erik,
Dyker Gerald
Publication year - 2006
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.200505411
Subject(s) - chemistry , alkylation , catalysis , selectivity , friedel–crafts reaction , reactivity (psychology) , chloride , organic chemistry , medicinal chemistry , medicine , alternative medicine , pathology
Abstract Gold chloride and BF 3 ⋅etherate were tested as Friedel–Crafts catalysts in the propargylation of electron‐rich arenes: differences in reactivity of the catalysts can be used to achieve high selectivity either for monoalkylation or for multiple alkylation products. In the case of a macrocyclization towards a heterocalixarene, gold catalysts exhibited a pronounced selectivity, whereas p ‐toluenesulfonic acid as catalyst opened up a competing pathway to a structural isomer.