Research ArticleChemistry

Electrochemical oxidation-induced etherification via C(sp3)─H/O─H cross-coupling

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Science Advances  15 May 2020:
Vol. 6, no. 20, eaaz0590
DOI: 10.1126/sciadv.aaz0590
  • Fig. 1 Previous etherification reactions and research scheme of this work.

  • Fig. 2 Substrate scope for the electrochemical etherification.

    Standard conditions: Carbon rod anode, nickel plate (15 mm by 15 mm by 1 mm) cathode, constant current = 10 mA, 1 (0.5 mmol), 2 (3 equiv.), nBu4NClO4 (0.5 equiv.), Cs2CO3 (2 equiv.), 20°C, in DCE/Et2O (6/0.5 ml) under N2 atmosphere for 3.5 hours, and an undivided cell. bDCE/DCM (4/2 ml). cCarbon rod anode, Pt plate (15 mm by 15 mm by 0.3 mm) cathode, in DCE (6 ml) under N2 atmosphere for 3.5 hours, 12°C.

  • Fig. 3 Control experiments.

    (A) Radical clock experiment. (B) Radical trapping experiment.

  • Fig. 4 Mechanistic studies.

    (A) Cyclic voltammograms of 0.01 M related compounds in 0.24 M nBu4NClO4 in DCE, using glass carbon working electrode, Pt wire as counter electrode, and Ag/AgCl as reference electrode at 50-mV/s scan rate. (B) EPR experiments.

  • Fig. 5 Proposed mechanism.

Supplementary Materials

  • Supplementary Materials

    Electrochemical oxidation-induced etherification via C(sp3)─H/O─H cross-coupling

    Huamin Wang, Kailun Liang, Wenpeng Xiong, Supravat Samanta, Wuqin Li, Aiwen Lei

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    • Figs. S1 and S2
    • Table S1
    • Spectroscopic data

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