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Synthesis 2015; 47(03): 395-410
DOI: 10.1055/s-0034-1379330
DOI: 10.1055/s-0034-1379330
paper
Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives
Further Information
Publication History
Received: 31 July 2014
Accepted after revision: 26 September 2014
Publication Date:
13 November 2014 (online)
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 (HOCH2SO2Na) 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.
Key words
hydrochalcogenation - buta-1,3-diynes - aryl dichalcogenides - rongalite - reductive cleavageSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379330.
- Supporting Information
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