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Transimination reactions in [b-3C-im][NTf2] ionic liquid†
Chao-Wen Chen,Ming-Chung Tseng,San-Kai Hsiao,Wen-Hao Chen,Yen-Ho Chu
Organic & Biomolecular Chemistry Pub Date : 03/25/2011 00:00:00 , DOI:10.1039/C0OB01094D
Abstract

Compared to conventional molecular solvents, the ionic liquid [b-3C-im][NTf2] was found to promote transimination reactions with up to ∼100-fold rate enhancement. This rate effect observed at ambient temperature might be explained by the fact that the ionic liquid displays weak Lewis acidity with very low, if any, nucleophilicity and its imidazolium cation is expected to interact by associating with, and thus electrophilically activating, the C[double bond, length as m-dash]N bond of the starting imine, leading to increased stabilization of the polar, charged intermediate species and ultimately, rapid product formation. Moreover, the presence of 1 mol% Sc(OTf)3 in [b-3C-im][NTf2] further facilitates the transimination reactions studied.

Graphical abstract: Transimination reactions in [b-3C-im][NTf2] ionic liquid
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