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Updated: May 15, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
Selective C-H activations using frustrated Lewis pairs. Applications in organic synthesis
Paul Knochel1, Konstantin Karaghiosoff, Sophia Manolikakes
1Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, Munich, Germany, Paul.Knochel@cup.uni-muenchen.de.
Abstract:
Frustrated Lewis pairs (FLPs), sterically encumbered Lewis acid and base combinations, gained importance due to their ability to activate molecular hydrogen. This property is used in organic synthesis to perform metal-free catalytic hydrogenation of imines, quinolines, or enamines. Moreover, it is possible to perform selective C-H activations using different sterically hindered Lewis acid/base pairs. Thus, the combination of organometallic reagents with different boranes can be used to functionalize selectively a variety of tertiary amines. By combination of sterically hindered metal amides of the type TMP-Met (TMP = 2,2,6,6-tetramethylpiperidyl, Met = Li, MgCl, ZnCl) with the Lewis-acid BF3·OEt2 it is possible to metalate selectively a large number of aromatic N-heterocycles, such as pyridines and quinolines.
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