Ryukichi Takagi, Y. Sakai, D. T. Duong
Mar 5, 2021
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Influential Citations
4
Citations
Journal
Tetrahedron
Abstract
A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Bronsted acid. Computational prediction of the pKa 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∙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.