Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Platinum-Catalyzed Reductive Aldol and Michael Reactions

  • Lee, Ha-Rim (Division of Energy Systems Research, Ajou University) ;
  • Jang, Min-Soo (Division of Energy Systems Research, Ajou University) ;
  • Song, Young-Jin (Division of Energy Systems Research, Ajou University) ;
  • Jang, Hye-Young (Division of Energy Systems Research, Ajou University)
  • Published : 2009.02.20
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Abstract

For the Pt-catalyzed nucleophilic addition of enones, Pt complexes were employed in the presence of various phosphine ligands and $H_2\;(or\;Et_3SiH),$ affording inter- and intra-molecular coupling products in good to modest yield. Depending on reaction protocols, different phosphine ligands were required to optimize the conditions. In the aldol reaction, the Pt catalyst involving $P(2,4,6-(OMe)_3C_6H_2)3\;or\;P(p-OMeC_6H_4)_3$ was chosen. Michael reaction proceeds in good yields in the presence of $P(p-CF_3C_6H_4)_3$. Regarding the activity of the reductants, $H_2$ exhibited superior activity to $Et_3SiH$, resulting in a shorter reaction time and higher yield in the aldol and Michael reaction. In light of the deuterium labeling studies, the catalytic cycle including the hydrometalation of the enones by the platinum hydride species was proposed.

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References

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