Highly Practical Synthesis of Nitriles and Heterocycles from Alcohols under Mild Conditions by Aerobic Double Dehydrogenative Catalysis

Weiyu Yin, Chengming Wang, and Yong Huang*

Org. Lett., 2013, 15, 1850–1853.

A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O₂. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.