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Synlett 2014; 25(09): 1287-1290
DOI: 10.1055/s-0033-1341240
DOI: 10.1055/s-0033-1341240
letter
Palladium Porphyrin Catalyzed Hydrogenation of Alkynes: Stereoselective Synthesis of cis-Alkenes
Weitere Informationen
Publikationsverlauf
Received: 27. Februar 2014
Accepted after revision: 24. März 2014
Publikationsdatum:
08. Mai 2014 (online)
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Abstract
(Tetraphenylporphyrin)palladium was developed as a catalyst for the chemoselective and stereoselective hydrogenation of alkynes to cis-alkenes by the syn-addition of hydrogen. Alkynes containing various functional groups were tolerated in the reaction, which gave the corresponding cis-alkenes in good to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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For selected examples of heterogeneous catalysts, see:
For examples of homogeneous catalysts, see:
We did not observed the formation of TPP as a result of demetalation of Pd(TPP) in the 1H NMR spectrum of the crude mixture. Despite this, the formation of Pd colloids as catalytically active species from the Pd(TPP) complex cannot be ruled out. Pd(TPP) might slowly release very small numbers of Pd atoms in situ to form catalytically highly active palladium colloids. For some examples of Pd nanoparticles stabilized by pyridines or their derivatives, see: