Monoalkylation of Acetonitrile by Primary Alcohols

The group of Cossy at CNRS, Paris in collaboration with the process development groups at Sanofi Aventis (Sisteron) has discovered a way to react primary alcohols with acetonitrile to produces extended nitriles in a very atom efficient reaction. (Org Lett, 2011, 13(15), 4084-7). Selectivity towards mono-alkylation is observed when using caesium carbonate and an iridium complex catalyst, though high temperatures are required. Benzyl alcohols with nitro, bromo or iodo groups were unsuccessful though chlorinated benzyl alcohols gave good yields.