Ind2TiMe2‐catalyzed addition of methyl‐ and ethylamine to alkynes

• Verfasst von: Marcseková, Klaudia [VerfasserIn]
• Verfasst von: Wegener, Bernd [VerfasserIn]
• Verfasst von: Doye, Sven [VerfasserIn]
• Titel: Ind2TiMe2‐catalyzed addition of methyl‐ and ethylamine to alkynes
• Verf.angabe: Klaudia Marcseková, Bernd Wegener, and Sven Doye
• E-Jahr: 2005
• Jahr: 3 November 2005
• Umfang: 9 S.
• Fussnoten: Gesehen am 21.03.2018
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Ort Quelle: Weinheim : Wiley-VCH Verl., 1998
• Jahr Quelle: 2005
• Band/Heft Quelle: (2005), 22, Seite 4843-4851
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/ejoc.200500458
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Alkynes
• Sach-SW: Amines
• Sach-SW: Homogeneous catalysis
• Sach-SW: Hydroamination
• Sach-SW: Titanium
• K10plus-PPN: 1571308091

Abstract

Abstract: We describe a very simple hydrogenation-like experimental protocol for the addition of gaseous methyl- and ethylamine to alkynes in the presence of Ind2TiMe2 as the catalyst. For efficient hydroamination reactions it is sufficient to stir a mixture of the alkyne and the catalyst in toluene at temperatures between 80 °C (terminal alkynes) and 105 °C (internal alkynes) under a constant pressure of 1 atm of the corresponding amine. After subsequent reduction of the initially formed imines, methyl- and ethylamine derivatives are the final products of the described one-pot reaction sequences. In the case of 2-alkyl-1-phenylalkynes as starting materials, biologically interesting 2-phenylethylamine derivatives possessing a small methyl or ethyl substituent at the N atom are easily accessible by the new reaction protocol.