Palladium-Catalyzed Decarbonylation of Acyl Cyanides

Article abstract of DOI:10.1021/jo00356a029

The palladium-catalyzed decarbonylation of aromatic and heteroaromatic acyl cyanides 1 gives the corresponding nitriles 2 in excellent yields.Alkylacyl cyanides can be converted into the corresponding alkenes via decarbonylation followed by β-elimination of hydrogen cyanide.Because of easy preparation of acyl cyanides by the oxidation of cyanohydrins, the present decarbonylation reaction provides an efficient method for the preparation of nitriles from aldehydes under mild and neutral conditions.The catalytic decarbonylation involves the following processes; oxidative addition of acyl cyanides 1 to Pd(PPh3)4 to give acylpalladium complexes 13, acyl-aryl rearrangement, reductive elimination.When an acyl cyanide has a β-hydrogen, the intermediate cyanoalkylcarbonylpalladium (15) undergoes β-elimination to give alkenes.