Nitriles are a versatile functional group in organic chemistry that are often intermediates in organic synthesis. Within this study we researched different methods in which nitrile groups are attached to different electrophiles through the use of organocuprate species. By optimizing conditions for the addition of a variety of organocopper complexes to a variety of electrophiles, a deeper understanding of nitrile and organocopper chemistry can be achieved. Throughout this study, reproducibility and reduction of waste were prioritized. As a starting point, we attempted to optimize our reactions with two main nucleophiles (acetonitrile, propionitrile, octanenitrile,) and different electrophiles (allyl bromide, geranyl diethyl phosphate, geranyl diphenylphosphinate, tosyl chloride, cinnamyl bromide, propargyl bromide, 1-iodonaphthalene, and β-bromostyrene). The products synthesized can be used in the synthesis of biologically active compounds.

Formation of nitriles through copper-mediated C–C bond formation

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ACS Fall 2022

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