Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives
Abstract This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH 2 SO 2 Na) and potassium carbonate, buta-1,3-diynes undergo stereoselect...
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Veröffentlicht in: | Synthesis (Stuttgart) 2014-11, Vol.47 (3), p.395-410 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | Abstract
This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH
2
SO
2
Na) and potassium carbonate, buta-1,3-diynes undergo stereoselective addition of the thiolate or selenide anion generated in situ from diaryl disulfides or diselenides to afford the corresponding (
Z
)-1-sulfanyl- or (
Z
)-1-selanylalk-1-en-3-yne derivatives, respectively. The reaction of buta-1,3-diynes with diaryl disulfides or diselenides at higher temperature (70 °C) gave a mixture of monothiolation/selenation and bisthiolation/selenation products in moderate to good yields. |
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ISSN: | 0039-7881 1437-210X |
DOI: | 10.1055/s-0034-1379330 |