Intramolecular hydroamination of alkynes catalysed by late transition metals

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Abstract
The cyclisation of 6-aminohex-1-yne to 2-methyl-1,2-dehydropiperidine in the presence of late transition metal catalysts was examined. The highest catalytic activity was observed for [Cu(CH3CN)4]PF6, as well as with Group 12 metal salts. Slightly lower conversions were obtained with the rhodium(I) and palladium(II) complexes [Rh(COD)(DiPAMP)]BF4 and [Pd(Triphos)][BF4]2. Catalysis was also observed with complexes of all group 9 to 12 metals and [Ru3(CO)12]. All catalytically active complexes contain a metal with a d8 or d10 electronic configuration. This observation allows preliminary conclusions about the mechanism to be made.