Transition-Metal- and Light-Free Generation of an Iminyl Radical: Facile Approach to Oxindoles and Isoquinolinediones with a Quaternary Carbon Center via Cyanoalkylarylation

Abstract

We have developed an efficient and non-toxic method for the environmental-friendly generation of an iminyl radical from cyclobutanone oxime ester via direct thermolysis in the absence of light, transition metals, "tin", and other activators. This redox-neutral cyanoalkylarylation protocol enjoys a wide substrate scope and a good functional group tolerance, providing facile access to oxindoles and isoquinolinediones with a quaternary carbon center that are difficult to prepare by traditional methods.