Research ArticleChemistry

Electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes with hydrogen evolution

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Science Advances  03 Aug 2018:
Vol. 4, no. 8, eaat5312
DOI: 10.1126/sciadv.aat5312
  • Fig. 1 Difunctionalization of alkenes.
  • Fig. 2 Mechanistic studies.
  • Fig. 3 Sampling experiment.

    Reaction conditions: C anode, Pt cathode, constant current = 12 mA, 1a (0.5 mmol), 2a (1.0 mmol), 3a (0.7 ml), nBu4NBF4 (3.0 mmol), MeCN (10 ml), 40°C, GC yields.

  • Fig. 4 Proposed mechanism.
  • Table 1 Substrate scope for alkene oxysulfenylation.

    Reaction conditions: C anode, Pt cathode, constant current = 12 mA, 1 (0.5 mmol), 2 (1.0 mmol), 3 [35 equivalent (equiv.)], nBu4NBF4 (3.0 mmol), MeCN (10 ml), 40°C, 4 hours, isolated yields.


    Embedded Image

    *Gram scale.

    †The yield was determined by 1H NMR spectroscopy, with CH2Br2 as the internal standard.

    ‡Diastereomeric ratio.

    §2 (5.0 equiv.).

    3 (1.0 ml of HOAc).

    3 (0.7 ml of H2O).

    • Table 2 Substrate scope for alkene aminosulfenylation.

      Reaction conditions: C anode, Pt cathode, constant current = 12 mA, 1 (0.5 mmol), 2 (1.0 mmol), 5 (1.0 mmol), nBu4NBF4 (0.5 mmol), MeCN (10 ml), 40°C, 4 hours, isolated yields.


      Embedded Image

      *5 (5.0 mmol).

      Supplementary Materials

      • Supplementary material for this article is available at http://advances.sciencemag.org/cgi/content/full/4/8/eaat5312/DC1

        Table S1. Optimization of reaction conditions.

        Fig. S1. The experimental setup for electrolysis.

        Section S1. Procedure for gram-scale synthesis

        Section S2. The cross-coupling experiment

        Section S3. Detailed descriptions for products

        Section S4. Copies of product NMR spectra

        References (48, 49)

      • Supplementary Materials

        This PDF file includes:

        • Table S1. Optimization of reaction conditions.
        • Fig. S1. The experimental setup for electrolysis.
        • Section S1. Procedure for gram-scale synthesis
        • Section S2. The cross-coupling experiment
        • Section S3. Detailed descriptions for products
        • Section S4. Copies of product NMR spectra
        • References (48, 49)

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