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Ind 2 TiMe 2 ‐Catalyzed Addition of Methyl‐ and Ethylamine to Alkynes
Author(s) -
Marcseková Klaudia,
Wegener Bernd,
Doye Sven
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500458
Subject(s) - chemistry , ethylamine , hydroamination , alkyne , catalysis , substituent , medicinal chemistry , amine gas treating , alkyl , organic chemistry , toluene
We describe a very simple hydrogenation‐like experimental protocol for the addition of gaseous methyl‐ and ethylamine to alkynes in the presence of Ind 2 TiMe 2 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)