Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics

Various open-chain and cyclic β-cyano zinc and copper organometallics can be prepared by the reaction of the corresponding organic halides with zinc and subsequent transmetalation with CuCN · 2 LiCl. They react in fair to good yields with various organic electrophiles (enones, allylic bromides and benzoyl chloride) affording highly functionalized nitriles. High diastereoselectivities have been observed in coupling reactions with the cyclic 2-cyano organocopper derivatives. The x-ray structure of cyanoethylzinc iodide is also reported.