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Published on: May 21, 2019
How Do Phosphinates React with Unactivated Alkenes Under Organic Photocatalyzed Conditions? Substrate Scope and
Giovanni Fausti1, Fabrice Morlet-Savary2, Jacques Lalevée2
1Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6, Boulevard Maréchal Juin, Caen, 14000, France.
Abstract:
The first visible-light-mediated, metal-free hydrophosphinylation of unactivated alkenes with ethyl and butyl phosphinates is described. The reaction works with a low catalyst loading of 9-mesityl-10-methylacridinium perchlorate (Fukuzumi photocatalyst, 0.5 mol %) in the presence of diphenyliodonium triflate as oxidant. The reaction proceeds smoothly and covers a broad scope of substrates. Detailed mechanistic investigations, including EPR spectroscopy, fluorescence and steady-state photolysis, allowed the mechanism of this photoreaction to be rationalized.
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