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A Surprising Substituent Effect Provides a Superior Boronic Acid Catalyst for Mild and Metal‐Free Direct Friedel–Crafts Alkylations and Prenylations of Neutral Arenes
Author(s) -
Ricardo Carolynne L.,
Mo Xiaobin,
McCubbin J. Adam,
Hall Dennis G.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500020
Subject(s) - friedel–crafts reaction , chemistry , substituent , catalysis , allylic rearrangement , commodity chemicals , boronic acid , organic chemistry , combinatorial chemistry
The development of more general and efficient catalytic processes for Friedel–Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5‐tetrafluorophenylboronic acid was identified as a potent air‐ and moisture‐tolerant metal‐free catalyst that significantly improves the scope of direct Friedel–Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.