Synthesis of Secondary Enamides by Ruthenium-Catalyzed Selective Addition of Amides to Terminal Alkynes†
Lukas J. Gooßen Prof. Dr.
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorKifah S. M. Salih
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorMathieu Blanchot
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorLukas J. Gooßen Prof. Dr.
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorKifah S. M. Salih
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorMathieu Blanchot
FB Chemie—Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany), Fax: (+49) 631-205-3921 http://www.chemie.uni-kl.de/goossen
Search for more papers by this authorWe thank the DFG and Umicore AG for financial support.
Graphical Abstract
Enamides made easy: A catalyst system generated in situ using bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate efficiently catalyzes the addition of primary amides to terminal alkynes, selectively forming the Z-anti-Markovnikov enamides. The E isomers are also accessible by combining the hydroamidation with an in situ double-bond isomerization reaction.
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