α-Aminocarbene-Mediated Si–H Insertion: Deoxygenative Silylation of Aromatic Amides with Silanes

Abstract

While metal carbene-mediated Si–H insertion reactions have become a powerful strategy to build new C–Si bonds, the utilization of α-aminocarbene intermediates generated from readily available precursors in the Si–H insertion reaction remains a longstanding challenge. Herein, we develop a practical and general strategy to synthesize α-aminosilanes through a deoxygenative cross-coupling of amides and silanes mediated by Sm/SmI2. Given the simplicity and versatility, this methodology represents a fascinating example for the effective utilization of inert amides as α-aminocarbene precursors in organic synthesis.

Topics & Concepts