Addition of thiols to phenylselenoalkynes using KF/Alumina under solvent-free conditions

We present herein the results of a simple and efficient protocol for the hydrothiolation of phenylselenoalkynes promoted by KF/Al2O3 using solvent-free conditions. This improved method furnishes selectively the corresponding (Z)-1-phenylseleno-2-organylthio-1-alkenes in reasonable to good yields sta...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2010, Vol.21 (11), p.2125-2129
Main Authors: Lara, Renata G, Borges, Elton L, Lenardão, Eder J, Alves, Diego, Jacob, Raquel G, Perin, Gelson
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:We present herein the results of a simple and efficient protocol for the hydrothiolation of phenylselenoalkynes promoted by KF/Al2O3 using solvent-free conditions. This improved method furnishes selectively the corresponding (Z)-1-phenylseleno-2-organylthio-1-alkenes in reasonable to good yields starting from selenoalkynes and aliphatic or aromatic thiols. The presence of the phenylselenium group in the alkyne directed the regiochemistry of the thiol addition. The catalytic system can be reused up to 4 times without previous treatment.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532010001100014