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Electrooxidative CH/PH functionalization as a novel way to synthesize benzo[b]phosphole oxides mediated by catalytic amounts of silver acetate

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Abstract

Electrochemical joint oxidation of diphenylphosphine oxide with acetylenes in the presence of silver acetate (10%) as a catalyst yields benzo[b]phosphole oxide derivatives under mild conditions at room temperature without additional oxidants or initiators and with yields up to 100%. The redox properties of the key intermediate of the catalytic cycle have been investigated by cyclic voltammetry and EPR spectroscopy. The Ph2P(O)Ag intermediate oxidizes easier (+0.05 V vs. Fc+/Fc) than all reaction precursors to form the phosphinyl radical Ph2P([double bond, length as m-dash]O)˙, fixed as a spin-adduct by ESR. Thus, a radical mechanism type through the Ag+/Ag0 couple was developed for electrocatalytic conditions.

Graphical abstract: Electrooxidative CH/PH functionalization as a novel way to synthesize benzo[b]phosphole oxides mediated by catalytic amounts of silver acetate

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Publication details

The article was received on 28 Sep 2017, accepted on 25 Nov 2017 and first published on 27 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03717A
Citation: New J. Chem., 2018, Advance Article
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    Electrooxidative CH/PH functionalization as a novel way to synthesize benzo[b]phosphole oxides mediated by catalytic amounts of silver acetate

    V. V. Khrizanforova, K. V. Kholin, M. N. Khrizanforov, M. K. Kadirov and Yu. H. Budnikova, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ03717A

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