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Amine-Borane Mediated Metal-Free Hydrogen Activation and Catalytic Hydrogenation

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Frustrated Lewis Pairs I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 332))

Abstract

The use of frustrated Lewis pairs (FLPs) as hydrogenation catalysts is attracting increasing attention as one of the most modern and rapidly growing areas of organic chemistry, with many research groups around the world working on this subject. Since the pioneering studies of the groups of Stephan and Piers on the Lewis acid–base pairs, which do not react irreversibly with each other and act as a trap for small molecules, numerous FLPs for hydrogen activation have been reported. Among others, intra- and intermolecular systems based on phosphines, organic carbenes, amines as Lewis bases, and boranes or alanes as Lewis acids were studied. This review presents a progression from the first observation of the facile heterolytical cleavage of hydrogen gas by amines and B(C6F5)3 to highly active non-metal catalysts for both enantioselective and racemic hydrogenation of unsaturated nitrogen-containing compounds and also internal alkynes.

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Abbreviations

1D NOE:

One-dimensional nuclear Overhauser effect spectroscopy

2D NOESY:

Two-dimensional nuclear Overhauser effect spectroscopy

9-BBN:

9-Borabicyclo[3.3.1]nonane

BCF:

Tris(pentafluorophenyl)borane

Bn:

Benzyl

Bu:

Butyl

d:

Day(s)

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DFT:

Density functional theory

DHB:

Dihydrogen bond

DMDPP:

trans-2,6-Dimethyl-2,6-diphenylpiperidine

ee:

Enantiomer excess

equiv.:

Equivalent(s)

Et:

Ethyl

FLP:

Frustrated Lewis pair

FT-IR:

Fourier transform infrared spectroscopy

h:

Hour(s)

iPr:

Isopropyl

ItBu:

1,3-Di-tert-butylimidazolin-2-ylidene

LAB:

Lewis acid–base

Me:

Methyl

Mes:

Mesityl 2,4,6-trimethylphenyl (not methanesulfonyl)

min:

Minute(s)

MTBE:

Methyl tert-butyl ether

NHC:

N-Heterocyclic carbene

NMR:

Nuclear magnetic resonance

Np:

Naphthyl

o-Tol:

o-Methylphenyl

Ph:

Phenyl

PMP:

p-Methoxyphenyl

Pr:

Propyl

RT:

Room temperature

tBu:

tert-Butyl

THF:

Tetrahydrofuran

TMP:

2,2,6,6-Tetramethylpiperidine

TMS:

Trimethylsilyl

Tos:

Tosyl 4-toluenesulfonyl

TRIP:

3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate

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Author information

Authors and Affiliations

  1. Borealis Polymers Oy, 330, 06101, Porvoo, Finland

    Victor Sumerin

  2. Department of Chemistry, University of Helsinki, 55, 00014, Helsinki, Finland

    Konstantin Chernichenko, Markku Leskelä & Timo Repo

  3. Clariant Produkte (Deutschland) GmbH, Waldheimer Straße 13, 83052, Bruckmühl, Germany

    Felix Schulz

  4. WACKER-Lehrstuhl für Makromolekulare Chemie, Technische Universität München, Lichtenbergstraße 4, 85747, Garching bei München, Germany

    Bernhard Rieger

Authors
  1. Victor Sumerin
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  2. Konstantin Chernichenko
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  3. Felix Schulz
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  4. Markku Leskelä
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  5. Bernhard Rieger
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  6. Timo Repo
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Correspondence to Bernhard Rieger or Timo Repo .

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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, Canada

    Douglas W. Stephan

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Sumerin, V., Chernichenko, K., Schulz, F., Leskelä, M., Rieger, B., Repo, T. (2012). Amine-Borane Mediated Metal-Free Hydrogen Activation and Catalytic Hydrogenation. In: Erker, G., Stephan, D. (eds) Frustrated Lewis Pairs I. Topics in Current Chemistry, vol 332. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2012_391

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