Catalytic Friedel-Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols

Vuk D Vuković; Edward Richmond; Eléna Wolf; Joseph Moran

doi:10.1002/anie.201612573

Catalytic Friedel-Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols

Angew Chem Int Ed Engl. 2017 Mar 6;56(11):3085-3089. doi: 10.1002/anie.201612573. Epub 2017 Feb 3.

Authors

Vuk D Vuković¹, Edward Richmond¹, Eléna Wolf¹, Joseph Moran¹

Affiliation

¹ University of Strasbourg, CNRS, ISIS UMR 7006, 67000, Strasbourg, France.

PMID: 28156038
DOI: 10.1002/anie.201612573

Abstract

Highly electronically deactivated benzylic alcohols, including those with a CF₃ group 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.

Keywords: Brønsted acid catalysis; Friedel-Crafts; alcohols; carbenium ion; hexafluoro-2-propanol.

Publication types

Research Support, Non-U.S. Gov't