Visible-Light-Induced Insertion of Siloxycarbene into Amide N-H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides

The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced insertion of siloxycarbene into amide N-H bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions with a broad range of secondary N-H amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable N- and O-acetals in excellent isolated yields. In addition, the chemoselective insertion reveals the robustness of this chemical transformation.