Ruthenium-Catalyzed α-Olefination of Nitriles Using Secondary Alcohols

Ruthenium(II) pincer-catalyzed α-olefination of nitriles is reported. This simple protocol provides a transformation for the catalytic synthesis of β-disubstituted vinyl nitriles using secondary alcohols. This catalytic method has an extensive substrate scope, as arylmethyl nitriles, heteroarylmethyl nitriles, and aliphatic nitriles as well as cyclic, acyclic, symmetrical, and unsymmetrical secondary alcohols are all employed in the reaction to provide diverse α-vinyl nitriles. C═C bond formation proceeds through activation of the O–H bond of secondary alcohols via an unsaturated 16-electron intermediate ruthenium pincer complex and further condensation of in situ-formed ketones with nitriles. Remarkably, H2 and H2O are the only byproducts of this method