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The Pauson–Khand Reaction

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Catalytic Carbonylation Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 18))

Abstract

The transition metal mediated conversion of alkynes, alkenes, and carbon monoxide in a formal [2 + 2 + 1] cycloaddition process, commonly known as the Pauson–Khand reaction (PKR), is an elegant method for the construction of cyclopentenone scaffolds. During the last decade, significant improvements have been achieved in this area. For instance, catalytic PKR variants are nowadays possible with different metal sources. In addition, new asymmetric approaches were established and the reaction has been applied as a key step in various total syntheses. Recent work has also focused on the development of CO-free conditions, incorporating transfer carbonylation reactions. This review attempts to cover the most important developments in this area.

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Abbreviations

acac:

Acetylacetonate

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

BSA:

Bis(trimethylsilyl)acetamide

Bu:

Butyl

tBu:

tert-Butyl

cod:

Cyclooctadiene

Cp:

Cyclopentadienyl

dba:

Dibenzylideneacetone

DMAc:

N,N-Dimethylacetamide

DME:

1,2-Dimethoxyethane

DMSO:

Dimethyl sulfoxide

dppb:

1,4-Bis(diphenylphosphino)butane

dppp:

1,3-Bis(diphenylphosphino)propane

EBTHI:

Ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)

ee:

Enantiomeric excess

Me:

Methyl

Ph:

Phenyl

PKR:

Pauson–Khand reaction

Py:

Pyridine

SDS:

Sodium dodecyl sulfate

Tf:

Trifluoromethanesulfonyl

TMANO:

Trimethylamine N-oxide

tolBINAP:

2,2′-Bis(di-4-tolylphosphino)-1,1′-binaphthyl

TPPTS:

Triphenylphosphine trisulfonate

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Authors and Affiliations

  1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany

    Dirk Strübing & Matthias Beller

Authors
  1. Dirk Strübing
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  2. Matthias Beller
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Correspondence to Matthias Beller .

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Matthias Beller

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© 2006 Springer-Verlag Berlin Heidelberg

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Strübing, D., Beller, M. (2006). The Pauson–Khand Reaction. In: Beller, M. (eds) Catalytic Carbonylation Reactions. Topics in Organometallic Chemistry, vol 18. Springer, Berlin, Heidelberg . https://doi.org/10.1007/3418_020

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