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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 2
BKCSDE 30(2)
February 20, 2009 

Platinum-Catalyzed Reductive Aldol and Michael Reactions
Harim Lee, Min Soo Jang, Young Jin Song, Hye Young Jang*
Platinum chloride, Reductive aldol reaction, Reductive Michael reaction
For the Pt-catalyzed nucleophilic addition of enones, Pt complexes were employed in the presence of various phosphine ligands and H2 (or Et3SiH), 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)3C6H2)3 or P(p-OMeC6H4)3 was chosen. Michael reaction proceeds in good yields in the presence of P(p-CF3C6H4)3. Regarding the activity of the reductants, H2 exhibited superior activity to Et3SiH, 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.
327 - 333
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