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2007
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In the Laboratory
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Formation of a Ruthenium–Arene Complex, Cyclometallation with a Substituted Benzylamine, and Insertion of an Alkyne
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Synthetic Experiments in Organometallic Chemistry
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Michael J. Chetcuti and Vincent Ritleng
Laboratoire de Chimie Organométallique Appliquée, UMR CNRS 7509, Ecole Européenne de Chimie, Polymères et Matériaux, Université Louis Pasteur, 67087 Strasbourg, France
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June 2007
Vol. 84 No. 6
p. 1014
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| Abstract |
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A three-part experiment that includes the synthesis of an arene complex, its cyclometallation, and an insertion reaction with the cyclometallated product is presented. The reaction of RuIIICl3⋅xH2O with 1,3-cyclohexadiene provides the ruthenium–arene complex [RuII(η6-C6H6)(µ-Cl)Cl]2. This is then allowed to react with N,N-dimethylbenzylamine to yield the cycloruthenated complex [RuII(η6-C6H6){2-(CH2NMe2)-C6H4}(CH3CN)](PF6), 2, by intra-molecular C–H activation. Reaction of the latter complex with diphenylacetylene affords the ruthenium(0) sandwich complex [Ru0(η6-C6H6)(η4-C6H4CH2NMe2CPh=CPh-1,2)](PF6), 3, after successive C–C and C–N coupling reactions. The sequence of experiments provides an excellent example of metal-mediated functionalization of a C–H bond and is appropriate for an advanced undergraduate or a graduate lab course. It also provides an opportunity for students to learn standard schlenk techniques. Furthermore, the characterization of the products by 1H NMR spectroscopy demonstrates the utility of 1H NMR not just in organic but also in organometallic chemistry.
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| Supplement |
A student handout containing detailed experimental procedures; notes for the instructor including spectral data for all products; and 1H NMR spectra of compounds 2 and 3 are available.
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| More Information |
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Citation |
Chetcuti, Michael J.; Ritleng, Vincent. J. Chem. Educ. 2007, 84, 1014.
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Keywords |
Alkynes; Amines / Ammonium Compounds; Chromatography; Graduate Education / Research; Hands-On Learning / Manipulatives; Inorganic Chemistry; Laboratory Instruction; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Organometallics; Ruthenium; Synthesis; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
4/24/2007
5/3/2007
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 Caution! | | Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations. |
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1014
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