119486-00-9Relevant articles and documents
Three-component synthesis of α-branched amines under barbier-like conditions
Le Gall, Erwan,Haurena, Caroline,Sengmany, Stephane,Martens, Thierry,Troupel, Michel
supporting information; experimental part, p. 7971 - 7973 (2010/02/28)
(Chemical Equation Presented) An array of α-branched amines has been prepared by using an expedient three-component Mannich-type reaction among organic halides, aldehyde derivatives, and amines. The experimental procedure, which is characterized by its simplicity, employs zinc dust for the in situ generation of organozinc reagents. We show that this Barbier-like protocol constitutes a useful entry to diarylmethylamines, 1,2-diarylethylamines, α- or β-amino esters, benzylamines, and β-arylethylamines.
Cp*2TiMe2: An improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes
Heutling, Andreas,Doye, Sven
, p. 1961 - 1964 (2007/10/03)
Cp*2TiMe2 has been found to be a competent catalyst for the intermolecular addition of sterically less demanding n-alkyl- and benzylamines to internal alkynes. In the presence of 2.0-6.0 mol % of the catalyst, hydroamination reactions between n-propyl-, n-hexyl-, benzyl-, p-methoxybenzyl- or 2-phenylethylamine and diphenylacetylene, 3-hexyne or 4-octyne go to completion within 24 h or less at 114°C (oil bath temperature). After subsequent reduction of the initially formed imines with zinc-modified sodium cyanoborohydride in MeOH at 25°C, the corresponding secondary amines can be isolated in excellent yields (> 78%). Hydroamination/reduction sequences employing the unsymmetrically substituted alkyne 1-phenylpropyne give access to mixtures of regioisomeric secondary amines. The observed regioselectivity is low.
