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Metal-free synthesis of 6‑phosphorylated phenanthridines: synthetic and mechanistic insights

Abstract : A novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenyliodonium salt (Ph2I+,–OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations, the mechanism of this reaction is discussed.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01847953
Contributor : Jocelyne Levillain <>
Submitted on : Tuesday, July 24, 2018 - 10:59:15 AM
Last modification on : Thursday, July 2, 2020 - 3:19:22 AM

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Ludovik Noël-Duchesneau, Elodie Lagadic, Fabrice Morlet-Savary, Jean-François Lohier, Isabelle Chataigner, et al.. Metal-free synthesis of 6‑phosphorylated phenanthridines: synthetic and mechanistic insights. Organic Letters, American Chemical Society, 2016, 18 (22), pp.5900-5903. ⟨10.1021/acs.orglett.6b02983⟩. ⟨hal-01847953⟩

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