The synthesis of 5-bromopenta-2,4-diynenitrile (BrC_5N) in three steps from commercially available compounds is reported. Reacting 5-bromopenta-2,4-diynenitrile with secondary amines led to the formation of stable butadiynamines or enynenitriles, depending on the nature of the amine reactant. The reaction of 5-bromopenta- 2,4-diynenitrile with simple terminal alkynes in the presence of secondary amines, copper, and palladium catalysts, provided a straightforward access to original polyfunctional carbon-rich scaffolds. In this work, different alkynes and secondary amines were tested, which allowed for the preparation of a family of substituted dienes. Given the high synthetic potential of 5-bromopenta-2,4-diynenitrile, we also prepared iodinated counterparts of this compound, that is, 5-iodopenta-2,4-diynenitrile and its lower homologue 3-iodopropiolonitrile. The UVvisible spectrum of some relevant compounds was also recorded.
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