Catalytic Friedel-Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols.
Highly electronically deactivated benzylic alcohols, including those with a CF3group adjacent to the OH-bearing carbon, undergo dehydrative Friedel-Crafts reactions upon exposure to catalytic Brønsted acid in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) solvent. Titration and kinetic experiments support the involvement of higher order solvent/acid clusters in catalysis.
University of Strasbourg, CNRS, ISIS UMR 7006, 67000, Strasbourg, France.
Vuk D
VD
Vuković
University of Strasbourg, CNRS, ISIS UMR 7006, 67000, Strasbourg, France.
Edward
0000-0001-8068-2379
E
Richmond
University of Strasbourg, CNRS, ISIS UMR 7006, 67000, Strasbourg, France.
Eléna
E
Wolf
University of Strasbourg, CNRS, ISIS UMR 7006, 67000, Strasbourg, France.
Joseph
0000-0002-7851-6133
J
Moran
Brønsted acid catalysis; Friedel-Crafts; alcohols; carbenium ion; hexafluoro-2-propanol