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External oxidant-free cross-coupling: electrochemically induced aromatic C–H phosphonation of azoles with dialkyl-H-phosphonates under silver catalysis

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Abstract

A convenient external oxidant-free method of phosphorylation of azole derivatives (benzo-1,3-azoles, 3-methylindole, 4-methyl-2-acetylthiazole) by using dialkyl-H-phosphonates through the catalytic oxidation of their mixture under electrochemical mild conditions (room temperature, normal pressure) in the presence of silver salts or oxide (1%) is proposed. This method allows us to obtain the desired azole dialkylphosphonates with good yield (up to 75%). The transformations of silver and phosphorus precursors and intermediates using cyclic voltammetry, ESR, and NMR spectroscopy were investigated, and a radical process mechanism was proposed. It has been found that AgP(O)(OEt)2 is oxidized earlier than other components of the reaction mixture with the elimination of a radical. The ESR spectrum of this radical's adduct was obtained in the presence of the radical trap PBN. Ag2+ is out of the catalytic cycle.

Graphical abstract: External oxidant-free cross-coupling: electrochemically induced aromatic C–H phosphonation of azoles with dialkyl-H-phosphonates under silver catalysis

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Publication details

The article was received on 28 Sep 2017, accepted on 18 Nov 2017 and first published on 21 Nov 2017


Article type: Paper
DOI: 10.1039/C7DT03650G
Citation: Dalton Trans., 2018, Advance Article
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    External oxidant-free cross-coupling: electrochemically induced aromatic C–H phosphonation of azoles with dialkyl-H-phosphonates under silver catalysis

    E. O. Yurko, T. V. Gryaznova, K. V. Kholin, V. V. Khrizanforova and Y. H. Budnikova, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C7DT03650G

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