Triflic Acid/Silane Promoted Deoxygenative Transformation of Ketones via Carbocations
Jianxin Hou, Xue Han⊗, Yiyi Zhang, Jiahui Huang, Jiawei Wang, Kedong Yuan
Abstract
Deoxygenative transformation of ketones into value-added products often suffers from precious-metal-based catalysts or complicated operational conditions. Triflic acid and silane serve as a cooperative reductant to transform ketones via carbocations that undergo β-H elimination much faster than hydride transfer from silane to produce alkenes with high selectivity. Alternatively, the presence of indoles would incept the protonated ketones to generate carbocations, allowing access to Csp 2 –Csp 3 bond formation with high reactivity and selectivity in “one pot”.
Topics & Concepts
Triflic acidCarbocationChemistrySilaneProtonationSelectivityHydrideCombinatorial chemistryCatalysisOrganic chemistryPhotochemistryMetalIonCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis