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Ind2TiMe2‐catalyzed addition of methyl‐ and ethylamine to alkynes

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 toluen...

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Hauptverfasser: Marcseková, Klaudia (VerfasserIn) , Wegener, Bernd (VerfasserIn) , Doye, Sven (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 3 November 2005
In: European journal of organic chemistry
Year: 2005, Heft: 22, Pages: 4843-4851
ISSN:1099-0690
DOI:10.1002/ejoc.200500458
Online-Zugang:Verlag, Pay-per-use, Volltext: http://dx.doi.org/10.1002/ejoc.200500458
Verlag, Pay-per-use, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200500458
Volltext
Verfasserangaben:Klaudia Marcseková, Bernd Wegener, and Sven Doye

MARC

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520 |a 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. 
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