Hydrocyanation - Inorganic Chemistry

Inorganic Chemistry

Hydrocyanation is performed on alkenes and alkynes with copper, palladium, and most commonly, nickel catalysts. Industrial hydrocyanation utilizes phosphite (P(OR)3) complexes of nickel. Phosphites give excellent catalysts, whereas the related phosphine (PR3) ligands, which are more basic, are catalytically inactive. Chiral, chelating aryl diphosphite complexes are commonly employed in asymmetric hydrocyanation. An example of a nickel–phosphite catalyzed hydrocyanation of ethene.

Lewis acids, such as B(C6H5)3, can increase hydrocyanation rates and allow for lower operating temperatures. Triphenylboron may derive this ability from sterically protecting the –CN as it is bound to nitrogen. Rates can also be amplified with electron–withdrawing groups (NO2, CF3, CN, C(=O)OR, C(=O)R) on the phosphite ligands, because they stabilize Ni(0). A major problem when using nickel catalysts for hydrocyanation is the production of Ni0(CN)x as a result of excess HCN.3 Bulky ligands impede the formation of these unreactive Ni0(CN)x complexes.

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