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Issue 32, 2014
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Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

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Abstract

Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields. Compared with the previous method, the present route is very simple, atom-economical and environmentally friendly.

Graphical abstract: Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

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Publication details

The article was received on 05 Jun 2014, accepted on 01 Jul 2014 and first published on 01 Jul 2014


Article type: Communication
DOI: 10.1039/C4OB01159G
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Org. Biomol. Chem., 2014,12, 6072-6075

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    Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

    C. He, X. Qian and P. Sun, Org. Biomol. Chem., 2014, 12, 6072
    DOI: 10.1039/C4OB01159G

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