An efficient electrochemical synthesis of phenylethynylcopper(I), C6H5CCCu

doi:10.1016/0022-328X(85)87134-5

Journal of Organometallic Chemistry

Volume 281, Issues 2–3, 19 February 1985, Pages c47-c48

https://doi.org/10.1016/0022-328X(85)87134-5 Get rights and content

Abstract

Phenylethynylcopper(I) can be prepared in high yield by the oxidation of a copper anode in a solution of phenylacetylene in acetone or acetonitrile. This synthesis represents a significant improvement over existing methods.

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Citation Excerpt :
These syntheses were carried out under inert atmosphere. The direct electrochemical syntheses of Cu(I) [321] or some other metallic acetylide complexes [322], and metallocenes [322] including ferrocene [323,324] were also presented. As explained before, the conditions for this kind of synthetic procedures are very gentle and they take place at atmospheric pressure and room temperature.
In this work, a compilation of electrochemically prepared metallic complexes is presented. All of them were synthesized by using a single step electrolytic process. This procedure is useful in the syntheses of homoleptic and heteroleptic complexes. Perhaps the most important point is the versatility of the proligands which can be used for the syntheses: a variety of functional groups and a number of coordination modes for the different ligands are reported.
However, unpredictable results were also obtained in some cases; these results were successfully interpreted and, many times, they were useful for new syntheses, both by using the results themselves or for the prevention against non desirable products. A summary of these unexpected situations is also presented.
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The article reviews the electrosynthesis of different kinds of coordination compound by the dissolution of sacrificial metal anodes into aqueous and non-aqueous media. The advantages of the method have been emphasized and a brief discussion on the mechanism has been included. The coverage of the literature is almost complete up to 1992 beginning from the early 1970s. In conclusion the article points out certain areas of electrosynthesis which deserve attention.
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The electrochemical oxidation of either zinc or cadmium (= M) in acetone solutions of o-C₆H₄(OH)₂ (= R(OH)₂) gives M(O₂R) in good yield. The advantages of this method are discussed. When neutral mono- or bidentate donors are present in the solution, the products are the 1:2 or 1:1 adducts of M(O₂R). Similar results ar reported for 2,3-dihydroxynaphthalene and 2,2′dihydroxybiphenyl. A preliminary crystal structure determination on Zn(O₂C₆H₄)(phen)₂·2C₆H₄(OH)₂ (phen) = 1.10-phenanthroline) shows the presence of a ZnO₂N₄ kernel; each oxygen atom of the catecholate ligand is hydrogen-bonded to both hydrogens of a neutral C₆H₄(OH)₂ molecule.
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Preliminary communicationAn efficient electrochemical synthesis of phenylethynylcopper(I), C6H5CCCu

Abstract

J. Organomet. Chem.

J. Gen. Chem. USSR

Preliminary communication
An efficient electrochemical synthesis of phenylethynylcopper(I), C₆H₅CCCu