Rhodium-Catalyzed Chemodivergent Synthesis of Organosilicons Enabled by Controllable C–Si Bond Activation

Abstract

Transition-metal-catalyzed C–Si bond activation has been emerging as a powerful tool for synthesizing organosilicons. However, chemodivergent synthesis of structurally diverse organosilicons via controllable C–Si bond activation remains challenging. Herein, we report a rhodium-catalyzed chemodivergent synthesis of organosilicons by controllable C–Si bond activation. This protocol enables the rapid synthesis of four types of organosilicons, including allyl silyl ethers, vinylsilanes, oxasilacycles, and β-silyl ketones, from simple silyl propargyl alcohols and arylboronic acids. The key to success is controllable on/off of the C–Si bond activation and selective cleavage of different types of C–Si bonds. This work demonstrates the possibility and great potential of controllable C–Si activation in transition-metal catalysis.

Rhodium-Catalyzed Hydrolytic Cleavage of the Silicon–Carbon Bond of Silacyclobutanes to Access Silanols

“…In the past several years, there has been a growing focus on the construction and cleavage of the silicon–carbon bond . This attention has been directed particularly toward the catalytic cleavage and transformations of silicon–carbon bonds in four-membered silacyclobutanes (SCBs) .…”