Photoinduced Synthesis of Functionalized Oxacyclic Spirooxindoles Via Ring Expansion

Abstract

A versatile photochemical ring-expansion protocol for the synthesis of oxacyclic spirooxindoles under catalyst-free conditions is described. The reaction is enabled by the use of unstrained O-containing heterocycles with 3-diazoindolin-2-ones under visible-light irradiation. Several synthetic advantages for this method are exhibited, including mild conditions, good functional group tolerance, operational simplicity, and scalability. Mechanistic studies indicate that the transformation may proceed through the formation of oxonium ylide intermediate followed by an ionic cyclization.