There have been numerous reports of bioactive compounds containing the 1, 3-diyne motif, as well as applications in organic synthesis. A compound containing this motif, known as Deblisone C, was discovered to have antimicrobial properties (Panthama et al. 2010). It was also found that this motif was used in the synthesis of 3, 5-disubstituted isoxazoles (Wang et al. 2012). Recently, our lab has developed a copper catalyzed reaction that synthesizes unsymmetrical and symmetrical 1, 3-diynes. We conducted experiments, in room temperature, with various copper compounds, as well as solvents, to determine the best reaction conditions for terminal alkyne homocoupling. We found that copper (II) triflate and acetone, were the optimal catalyst and solvent, respectively,ss for the homocoupling reaction of phenylacetylene. We then expanded our substrate scope, using copper (II) triflate and acetone, to other terminal alkynes, conducting several homocoupling and hetercoupling reactions.

Copper catalyzed homocoupling and heterocoupling of terminal alkynes

256th National Meeting (2018)

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