Research ArticleORGANIC CHEMISTRY

Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine

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Science Advances  09 Oct 2015:
Vol. 1, no. 9, e1500656
DOI: 10.1126/sciadv.1500656

Supplementary Materials

  • Supplementary material for this article is available at http://advances.sciencemag.org/cgi/content/full/1/9/e1500656/DC1

    General information

    General procedure

    Table S1. The evaluation of several metal salts.

    Table S2. The effects of other solvents.

    Table S3. The effects of reaction temperature.

    Table S4. The effects of the ratio of substrates.

    Table S5. The effects of LiCl loading.

    Table S6. Oxidative C–H/N–H coupling between ketone and ethylenediamine under standard reaction conditions.

    Scheme S1. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2a.

    Scheme S2. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2e.

    EPR experiments

    Radical trapping experiments

    Scheme S3. Radical trapping experiment using BHT [2,6-bis(1,1-dimethylethyl)-4-methylphenol] as the scavenger.

    Scheme S4. Radical trapping experiment using TEMPO (2,2,6,6-tetramethylpiperidinyloxy) as the scavenger.

    XAS experiments

    General computational calculation details

    Detailed descriptions for products

    NMR data

    References (6573)

  • Supplementary Materials

    This PDF file includes:

    • General information
    • General procedure
    • Table S1. The evaluation of several metal salts.
    • Table S2. The effects of other solvents.
    • Table S3. The effects of reaction temperature.
    • Table S4. The effects of the ratio of substrates.
    • Table S5. The effects of LiCl loading.
    • Table S6. Oxidative C–H/N–H coupling between ketone and ethylenediamine under standard reaction conditions.
    • Scheme S1. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2a.
    • Scheme S2. Gas chromatography–mass spectrometry analysis of the reaction between 1a and 2e.
    • EPR experiments
    • Radical trapping experiments
    • Scheme S3. Radical trapping experiment using BHT 2,6-bis(1,1-dimethylethyl)-4-methylphenol as the scavenger.
    • Scheme S4. Radical trapping experiment using TEMPO (2,2,6,6-tetramethylpiperidinyloxy) as the scavenger.
    • XAS experiments
    • General computational calculation details
    • Detailed descriptions for products
    • NMR data
    • References (65–73)

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    Files in this Data Supplement:

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