Access to Cyclopentenone via Pd(0)-Catalyzed Reductive Cyclization of (Z)-5-Iodo-4-pentenenitrile

A ligand-free Pd(0)-catalyzed cyclization of (Z)-5-iodo-4-pentenenitrile has been realized with the help of HCO2H reductant, which is followed by imine hydrolysis to afford cyclopentenone derivatives in moderate to good yields. Control experiments clearly points out that the proton originally came from HCO2H plays a crucial role on protonation of the resultant imido-Pd2+ intermediate. This protocol features mild condition, operational simplicity, as well as wide functional group tolerance.