Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Brønsted acid catalyst. (9th April 2021)

• Record Type: Journal Article
• Authors: Takagi, Ryukichi; Sakai, Yuichiro; Duong, Duyen Thi
• Is Part Of: Tetrahedron. Volume 85(2021)
• Publication Date: 2021-04-09
• Subjects: Brønsted acid -- Sulfonimide -- Hydroamination -- Hydroalkoxylation -- HFIP; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132037
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Brønsted acid. Computational prediction of the p K a value of BSI indicated its classification as a strong Brønsted acid. BSI catalyzed the hydroamination of alkenyl amines in hexafluoroisopropanol (HFIP) with efficiency comparable to that of TsOH∙H2 O, Tf2 NH, 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. Graphical abstract: To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. Leave this area blank for abstract info. Image 1 Highlights: A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Brønsted acid. Computational prediction of the p K a value of BSI indicated its classification as a strong Brønsted acid. BSI catalyzed the hydroamination of alkenyl amines in HFIP with efficiency comparable to that of TsOH∙H2 O, Tf2 NH, and TfOH.