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Preparation and Reactivity of Organomanganese Compounds

Organomanganese Compounds (2011)

  1. Gérard Cahiez,
  2. Olivier Gager

Published Online: 15 NOV 2010

DOI: 10.1002/9780470682531.pat0539

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Cahiez, G. and Gager, O. 2010. Preparation and Reactivity of Organomanganese Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. Laboratoire de Synthèse Organique Sélective et de Chimie Organométallique (SOSCOM), FRE 3043 CNRS-Université Paris13, Bobigny, France

Publication History

  1. Published Online: 15 NOV 2010

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Abstract

This chapter deals with the preparation of organomanganese reagents from organolithium or organomagnesium compounds (transmetallation) as well as from organic halides and manganese metal (oxidative addition). The influence of various parameters on the stability of organomanganese reagents is then discussed (nature of the reagent RMnX, R2Mn, R3MnLI or R3MnMgX; effect of ligands and solvents…). The second part of the chapter is devoted to the reactivity of these reagents and to their uses in organic synthesis. They are especially interesting for their chemoselectivity, as illustracted by the addition to aldehydes and ketones, the preparation of ketones by acylation or the copper-catalyzed conjugate addition to enones, enals and enoates. Organomanganese reagents can also be used to perform various iron, palladium or nickel-catalyzed cross-coupling reactions. Manganese salts are efficient catalyst to achieve various homo- and heterocoupling reactions using Grignard reagents. They are also used to catalyze the addition of Grignard reagents to acetylenes, 1,3-dienes and allenes. Finally, various radical cyclization reactions promoted by organomanganates are presented.

Keywords:

  • organomanganese reagents;
  • acylation;
  • 1,2-addition;
  • conjugated addition;
  • chemoselectivity;
  • cross-coupling reactions;
  • manganese-catalysis;
  • copper catalysis;
  • iron-catalysis

Featured Compounds

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  1. 1 - 6
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound IPrHCl
Molecular Weight:425.049
Molecular Formula:C27H37ClN2
InChIKey:AVJBQMXODCVJCJ-UHFFFAOYSA-M
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Compound A
Molecular Weight:324.078
Molecular Formula:C12H19Cl2LiMnN2
InChIKey:IUODTQVJPNPULW-UHFFFAOYSA-L
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Compound 12
Molecular Weight:117.72
Molecular Formula:ClH3MgMn
InChIKey:GBDODQPPRUTOIW-UHFFFAOYSA-M
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