Solvent-Controlled Silver Catalyzed Radical Transformation of α-Imino-Oxy Acids with Cyclic Aldimines

Abstract

A silver-catalyzed cross coupling of cyclic aldimines and α-imino-oxy acids has been developed. The solvent-dependent reaction could selectively deliver either cyclic imine moiety retained nitriles or ring-opened oxonitriles in moderate to good yields, each of which are synthetic important building blocks inaccessible by classical one-step procedures. The mechanistic studies show that the reaction undergoes a radical pathway in which an iminyl radical intermediate is involved, followed by β-carbon scission and trapping to give the remote functionalized nitriles.