Electrochemical C–H silylation of azauracils with hydrosilanes

Abstract

Polysubstituted azauracils represent highly important nitrogen-containing heterocyclic compounds that are widely found in biologically active molecules. Current synthetic methods primarily rely on expensive transition metals or often toxic photocatalysts to achieve CH functionalization of azauracils, making it imperative to develop simpler and more practical synthetic approaches. Electroorganic synthesis offers an excellent alternative strategy. Herein, we disclose an electrochemical CH silylation method for the synthesis of various silicon-substituted azauracils using azauracils and hydrosilanes as starting materials. This transformation is conducted in an undivided cell, offering operational simplicity, excellent substrate compatibility, and scalability to gram-scale synthesis. Furthermore, this strategy enables the late-stage derivatization of valuable molecules. Mechanistic studies reveal that azauracils capture silicon radicals through three distinct pathways, ultimately generating diverse polysubstituted azauracil derivatives.