N-methyl-benzothiazolium salts as carbon Lewis acids for Si-H σ bond activation and catalytic (de)hydrosilylation

Research output: Contribution to journalArticle

Abstract

N−Me-Benzothiazolium salts are introduced as a new family of Lewis acids able to activate Si−H σ bonds. These carbon-centred Lewis acids were demonstrated to have comparable Lewis acidity towards hydride as found for the triarylboranes widely used in Si−H σ-bond activation. However, they display low Lewis acidity towards hard Lewis bases such as Et3PO and H2O in contrast to triarylboranes. The N−Me-benzothiazolium salts are effective catalysts for a range of hydrosilylation and dehydrosilylation reactions. Judicious selection of the C2 aryl substituent in these cations enables tuning of the steric and electronic environment around the electrophilic centre to generate more active catalysts. Finally, related benzoxazolium and benzimidazolium salts were found also to be active for Si−H bond activation and as catalysts for the hydrosilylation of imines.

Bibliographical metadata

Original languageEnglish
JournalChemistry: A European Journal
Volume23
Issue number1
Early online date22 Nov 2016
DOIs
StatePublished - 2017