Nucleophilic Carbon Question

Question

Would KCN and (CH3)2CuLi be considered structures that have a nucleophilic carbon in them?

Answer 1

The short answer is "yes". The cyanide anion in KCN is a decent nucleophile, primarily for Sn2-type reactions, while dialkyl cuprates are fairly potent C-nucleophiles, although not as reactive as their organolithium or Grignard cousins. These cuprates are very useful in synthesis in that they tend to react in a 1,4-addition manner to conjugated enones, as opposed to rxn at the carbonyl.