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Selective C–H Activations Using Frustrated Lewis Pairs. Applications in Organic Synthesis

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Frustrated Lewis Pairs II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 334))

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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Abbreviations

A:

Lewis acid

B:

Lewis base

dba:

trans,trans-Dibenzylideneacetone

E:

Electrophile

Eq:

Equation

FLP:

Frustrated Lewis pair

Mes:

2,4,6-Trimethylphenyl

Met:

Metal

Nu:

Nucleophile

TBS:

tert-Butyldimethylsilyl

tfp:

Tris-(2-furyl)phosphine

TMP:

2,2,6,6-Tetramethylpiperidyl

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Authors and Affiliations

  1. Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, Munich, Germany

    Paul Knochel, Konstantin Karaghiosoff & Sophia Manolikakes

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  1. Paul Knochel
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  2. Konstantin Karaghiosoff
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  3. Sophia Manolikakes
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Correspondence to Paul Knochel .

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Editors and Affiliations

  1. Organisch-Chemisches Institut, Universität Münster, Corrensstr. 40, Münster, 48149, Germany

    Gerhard Erker

  2. , Department of Chemistry, University of Toronto, St. George Street 80, Toronto, M5S 3H6, Ontario, Canada

    Douglas W. Stephan

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Knochel, P., Karaghiosoff, K., Manolikakes, S. (2013). Selective C–H Activations Using Frustrated Lewis Pairs. Applications in Organic Synthesis. In: Erker, G., Stephan, D. (eds) Frustrated Lewis Pairs II. Topics in Current Chemistry, vol 334. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2012_394

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