Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Bronsted acid catalyst

A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Bronsted acid. Computational prediction of the pK(a) value of BSI indicated its classification as a strong Bronsted acid. BSI catalyzed the hydroamination of alkenyl amines in hexafluoroisopropanol (HFIP) with efficiency comparable to that of TsOH center dot H2O, Tf2NH, and TfOH. The adjacent sulfonimide groups on BSI were important for enhancing acidity. BSI additionally catalyzed the hydroalkoxylation of alkenyl alcohols in HFIP with high efficiency. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A binaphthyl derivative with bis(trifluoromethanesulfonimide) (BSI) moiety was developed as a novel Bronsted acid, showing strong acidity in computational prediction. BSI efficiently catalyzed the hydroamination of alkenyl amines and hydroalkoxylation of alkenyl alcohols in HFIP, with adjacent sulfonimide groups playing a crucial role in enhancing acidity.