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Borane-Catalyzed Divergent Hydrogenative and Silylative Reduction of Quinolinium Salts
Runze Luan1,2, Xiangqing Feng1,2, Haifeng Du1,2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing100190, P. R. China.
Abstract:
A B(C6F5)3-catalyzed chemoselective reduction of quinolinium salts was developed. This method afforded two distinct products in good to high yields by solvent modulation. In 1,4-dioxane, the reaction proceeds selectively to silylative reduction products, whereas in 1,2-dichloroethane, it gives direct hydrogenative reduction products. The selectivity may depend on the stability of silylium cations, which determines whether the key enamine intermediate undergoes silylation or protonation to form different products.
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