Issue 13, 2024

Acid–solvent cluster-catalyzed general and regioselective Friedel–Crafts arylation of alcohols

Abstract

Friedel–Crafts alkylation is among the oldest and most efficient strategies for C–H functionalization of arenes with a profound impact in both academia and industry. Despite significant advancements over the past 140 years, the extremely poor regioselectivity has greatly limited the broad application of the reaction. Herein, we disclose a general and highly regioselective Friedel–Crafts alkylation catalyzed by trifluoromethanesulfonic acid–hexafluoroisopropanol clusters, thereby providing various di- or polysubstituted arenes that previously were inaccessible or required elaborate synthetic efforts. Control experiments combined with DFT calculations suggest that the reaction involves a remarkable SN1-type event and the use of acid–solvent clusters is the key factor in achieving regioselectivity.

Graphical abstract: Acid–solvent cluster-catalyzed general and regioselective Friedel–Crafts arylation of alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
29 Mar 2024
Accepted
11 May 2024
First published
13 May 2024

Org. Chem. Front., 2024,11, 3602-3608

Acid–solvent cluster-catalyzed general and regioselective Friedel–Crafts arylation of alcohols

W. Fu, J. Fu, X. Wang, Y. Ding, Y. Li, J. Tian, J. Zhao, M. Wang and Z. Wang, Org. Chem. Front., 2024, 11, 3602 DOI: 10.1039/D4QO00555D

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