Catalytic conjugate addition of cyanide to enones:: Cooperative catalysis of Ni(0) and Gd(OTf)3

An efficient, synthetically useful catalytic cunjugate addition of cyanide to enones was developed using cooperative catalysis of Ni(0) and Gd(OTf)(3). The co-catalyst, Gd(OTf)(3), dramatically accelerated the reaction. The Substrate scope is broad, including cyclic, linear, branched, and aromatic enones. Synthetic efficiency of the key conversion in Our Tamiflu synthesis, conjugate cyanation of an enone, was significantly improved by using this new method. Gadolinium triflate is supposed to facilitate the oxidative addition of Ni(0) to enones, which constitutes a key step in the catalytic cycle.