Fast, ligand- and solvent-free synthesis of 1,4-substituted buta-1,3-diynes by Cu-catalyzed homocoupling of terminal alkynes in a ball mill |
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Authors: | Schmidt Robert Thorwirth Rico Szuppa Tony Stolle Achim Ondruschka Bernd Hopf Henning |
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Affiliation: | Institute for Technical Chemistry and Environmental Chemistry, Friedrich-Schiller University Jena, Lessingstrasse 12, 07743 Jena, Germany. |
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Abstract: | A method for the Glaser coupling reaction of alkynes by using a vibration ball mill has been developed. The procedure avoids the use of ligands and solvents during the reaction. Aryl- and alkyl-substituted terminal alkynes undergo homocoupling if coground with KF-Al(2)O(3) and CuI as a milling auxiliary and catalyst. Furthermore, an alternative protocol has been developed incorporating 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additional base allowing the use of KF-Al(2)O(3) with a lower KF loading. Besides Cu salts, the homocoupling of phenylacetylene is also catalyzed by Ni or Co salts, as well as by PdCl(2). TMS-protected phenylacetylene could be directly converted into the homocoupling product after in situ deprotection of the alkyne by fluoride-initiated removal of the trimethylsilyl group. |
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Keywords: | alkynes ball milling copper cross‐coupling homocoupling materials science |
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