Metal-free enaminone C-N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones

A highly practical method for C-CN bond formation by C-N bond cleavage on enaminones leading to the efficient synthesis of beta-cyano enones is developed. The reactions take place efficiently to provide (E)-beta-cyano enones with only a molecular iodine catalyst. In addition, the additional employment of oxalic acid enables the selective synthesis of (Z)-beta-cyano enones.

Automated summary

The highly practical method involves the cleavage of C-N bonds on enaminones for the formation of C-CN bonds, leading to efficient synthesis of beta-cyano enones with molecular iodine catalyst. Furthermore, oxalic acid can be employed for the selective synthesis of (Z)-beta-cyano enones.