Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3-Diynes |
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Authors: | Dr. Jiawang Liu Ji Yang Carolin Schneider Prof. Dr. Robert Franke Dr. Ralf Jackstell Prof. Dr. Matthias Beller |
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Affiliation: | 1. Leibniz-Institut für Katalyse, Albert-Einstein-Straße 29a, 18059 Rostock, Germany;2. Leibniz-Institut für Katalyse, Albert-Einstein-Straße 29a, 18059 Rostock, Germany These authors contributed equally to this work.;3. Evonik Performance Materials GmbH, Paul-Baumann-Str. 1, 45772 Marl, Germany Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum, Germany |
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Abstract: | For the first time, the monoalkoxycarbonylation of easily available 1,3-diynes to give synthetically useful conjugated enynes has been realized. Key to success was the design and utilization of the new ligand 2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos), which permits the palladium-catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3-enynes in good-to-high yields with excellent chemoselectivities. Synthetic applications that showcase the possibilities of this novel methodology include an efficient one-pot synthesis of 4-aryl-4H-pyrans as well as the rapid construction of various heterocyclic, bicyclic, and polycyclic compounds. |
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Keywords: | Konjugierte Enine Monocarbonylierung P-Liganden Palladium Selektivität |
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