90496-18-7

Upstream product

• 90496-15-4 But-(E)-ylidene-phenethyl-amine 
• 1942-45-6 4-Octyne 
• 64-04-0 phenethylamine 
• 109-65-9 1-bromo-butane 

Relevant academic research and scientific papers

Cp*2TiMe2: An improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes

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.

ADDITION OF BORON TRIFLUORIDE COMPLEXES OF ORGANOCOPPER REAGENTS TO ALDIMINES CONTAINING α-HYDROGENES

RCu*BF3, generated in situ from Grignard reagents, CuI, and BF3*OEt2, added to aldimines containing α-hydrogens to afford secondary amines in good yields.Boron trifluoride complex of dialkylcuprate gave essentially the same result with wider application.