Photoredox/Ti Dual-Catalyzed Dehydroxylation of Cyclobutanone Oximes for γ-Cyanoalkyl Radical Generation: Access to Cyanoalkyl-Substituted Oxoindolines

In this work, we have established a photoredox/Ti dual-catalyzed dehydroxylation of cyclobutanone oximes. The resulting gamma-cyanoalkyl radicals undergo a cascade radical addition/cyclization with N-acrylamides to afford cyanoalkyl substituted oxoindolines under mild conditions. This reaction also exhibits broad substrate scope and good functional group tolerance. Furthermore, it is applicable to late-stage functionalization of complex molecules and gram-scale synthesis, which illustrates its potential value in organic synthesis.

Automated summary

In this work, a photoredox/Ti dual-catalyzed dehydroxylation of cyclobutanone oximes has been established. The reaction proceeds under mild conditions, resulting in the formation of cyanoalkyl-substituted oxoindolines through a cascade radical addition/cyclization with N-acrylamides. The reaction shows broad substrate scope, good functional group tolerance, and can be used for late-stage functionalization of complex molecules and gram-scale synthesis, highlighting its potential value in organic synthesis.