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The hydroamination of terminal alkynes (RC CH = phenylacetylene, 4-methylphenylacetylene, 4-fluorophenylacetylene, 1-hexyne, methyl 2propynyl ether, prop-2-yn-1-ol) with secondary amines (piperidine, pyrrolidine, morpholine, piperazine, methylpiperazine, 4-methylpiperidine and 3methylpiperidine) was achieved in high yield (up to 99%), regioselectivity (only anti-Markovnikov product) and stereoselectivity (only E-isomers) within a maximum of 5 h in reactions catalyzed by the tungsten tetracarbonyl complex cis-[W(CO) 4 (piperidine) 2 ] at 908C without any additional solvent.

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Efficient and Selective Synthesis of E-Vinylamines via Tungsten(0)-Catalyzed Hydroamination of Terminal Alkynes. -The title reaction applies to both terminal arylalkynes and alkylalkynes, but alkylalkynes gives poor to moderate yields [e.g. (IV)]. The reaction is limited to secondary amines because the primary amines show very low reactivity under comparable reaction conditions. -(KOCIECKA, P.; CZELUSNIAK, I.; SZYMANSKA-BUZAR*, T.; Adv. Synth. Catal. 356 (2014) 16, 3319-3324, http://dx.doi.org/10.1002/adsc.201400568 ; Fac. Chem., Univ. Wroclaw, PL-50-383 Wroclaw, Pol.; Eng.) -L. Grundl 16-054