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ABSTRACT
This article describes the preparation of organometallic reagents of magnesium and zinc and their use in continuous flow. With the help of metalations of aromatic and heterocyclic ring systems, it was possible to prepare organo-magnesium and –zinc species difficult to obtain in batch. The remarkable compatibility of lithium bases with numerous metallic salts has allowed developing numerous procedures in continuous flow. A variation of this method involving a halogen-lithium exchange in the presence of metallic salts in continuous flow is also described as well as metalation procedures using sodium bases allowing to generate functionalized organo-sodium reagents.
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Read the articleAUTHORS
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Paul KNOCHEL: Professor of organometallic chemistry - Dr. in Chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
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Niels WEIDMANN: M.Sc. Chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
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Maximilian GANIEK: Dr. in organometallic chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
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Johannes HARENBERG: M.Sc. Chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
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Benjamin HEINZ: M.Sc. Chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
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Alexandre DESAINTJEAN: Chemical engineer and M.Sc. in molecular chemistry - Ludwig-Maximilians-Universität, Department Chemie und Biochemie, - Butenandtstr. 5-13, D-81377 München, Germany
INTRODUCTION
Organometallic compounds, which are molecules with a carbon-metal bond, are an important class of nucleophilic reagents in organic chemistry. Whether in terms of their properties and/or their reactivity, which can be modulated by the choice of metal, they present a vast field of application in organic synthesis. While the nature of the metal bonded to the carbon is essential for assessing their reactivity, the toxicity and price of the metal are equally important factors in the choice of the optimum metal. Taking all these aspects into account, the choice of organomagnesiums and organozincs as nucleophilic reagents is a natural one. These two metals combine good reactivity, compatibility with the various functional groups used in organic synthesis, low toxicity and affordability. This article describes the preparation of polyfunctionalized organometallic species and the use of these reagents for transformations in fine organic chemistry. The metals used in these reactions are mainly magnesium and zinc, but we also describe a few reactions using lithium or sodium, which are also relatively inexpensive and toxic compared with most of the metals normally used in organic chemistry. They can therefore easily be used in reactions carried out on an industrial scale, and present a definite ecological interest, whether in batch reactors or, as here, in flow chemistry.
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KEYWORDS
zinc | metalation | magnesium
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Unit operations. Chemical reaction engineering
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Continuous flow organometallic chemistry
Preparation of polyfunctionalized organometallic species
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