Metal-free photocatalyzed allylic silylation of allyl acetates and chlorides

Abstract

Allylsilanes are synthetically valuable building blocks for the synthesis of natural products and pharmaceuticals due to their high stability and low toxicity. However, conventional methods for synthesizing allylsilanes require stoichiometric metal reagents or toxic transition-metal catalysts. Herein, we present a visible light-induced organophotocatalytic strategy for synthesizing functionalized allylsilanes through radical allylic silylation of allyl acetates and chlorides. This approach eliminates the need for metal reagents or catalysts. To achieve this, bench-stable silacarboxylic acids were used as silyl radical precursors through efficient visible-light-induced decarboxylation. The protocol successfully produced a range of functionalized allylsilanes in good yields with high stereoselectivity. Additionally, a gram-scale reaction demonstrated the potential of this environmentally benign method for practical applications.