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http://dx.doi.org/10.5012/bkcs.2009.30.2.327

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)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.2, 2009 , pp. 327-333 More about this Journal
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.
Keywords
Platinum chloride; Reductive aldol reaction; Reductive Michael reaction;
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1 Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271   DOI   ScienceOn
2 Liu, C.; Bender, C. F.; Han, X.; Widenhoefer, R. A. Chem. Commun. 2007, 3607
3 Michelet, V.; Toullec, P. Y.; Genêt, J.-P. Angew. Chem. Int. Ed. 2008, 47, 4268   DOI   ScienceOn
4 Jiang, X.-b.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Org. Chem. 2004, 69, 2327   DOI   ScienceOn
5 Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649   DOI   ScienceOn
6 Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700   DOI   ScienceOn
7 Qian,H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536   DOI   ScienceOn
8 Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070   DOI   ScienceOn
9 Bigeault, J.; Giordano, L.; de Riggi, I.; Gimbert, Y.; Buono, G. Org. Lett. 2007, 9, 3567   DOI   ScienceOn
10 Itazaki, M.; Nishihara, Y.; Osakada, K. J. Org. Chem. 2002, 67, 6889   DOI   ScienceOn
11 Sprengers, J. W.; Mars, M. J.; Duin, M. A.; Cavell, K. J.; Elsevier, C. J. J. Organomet. Chem. 2003, 679, 149   DOI   ScienceOn
12 Behr, A.; Naendrup, F.; Obst, D. Adv. Synth. Catal. 2002, 344, 1142   DOI   ScienceOn
13 Buisine, O.; Berthon-Gelloz, G.; Brière, J.-F.; Stérin, S.; Mignani, G.; Branlard, P.; Tinant, B.; Declercq, J.-P.; Markó, I. E. Chem. Commun. 2005, 3856
14 De Bo, G.; Berthon-Gelloz, G.; Tinant, B.; Markó, I. E. Organometallics 2006, 25, 1881   DOI   ScienceOn
15 Diez-Gonzalez, S.; Blanco, L. J. Organomet. Chem. 2008, 693, 2033   DOI   ScienceOn
16 Cramer, R. D.; Lindsey, Jr. R. V.; Prewitt, C. T.; Stolberg, U. G. J. Am. Chem. Soc. 1965, 87, 658
17 Cramer, R.; Linsey, Jr. R. V. J. Am. Chem. Soc. 1966, 88, 3534   DOI
18 Clark, H. C.; Tsang, W. S. J. Am. Chem. Soc. 1967, 89, 529   DOI
19 Clark, H. C.; Dixon, K. R.; Jacobs, W. J. J. Am. Chem. Soc. 1969, 91, 1346   DOI
20 Clark, H.C.; Kurosawa, H. Inorg. Chem. 1972, 11, 1275   DOI
21 Clark, H. C.; Kurosawa, H. Inorg. Chem. 1973, 12, 357   DOI
22 Holt, M. S.; Wilson, W. L.; Nelson, J. H. Chem. Rev. 1989, 89, 11   DOI
23 Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G.; Hegedus, L. S. Organometallics 1991, 10, 1183   DOI
24 Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. J. Org. Chem. 2006, 71, 4255   DOI   ScienceOn
25 Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385   DOI   ScienceOn
26 Wang, X.; Chakrapani, H.; Madine, J. W.; Keyerleber, M. A.; Widenhoefer, R. A. J. Org. Chem. 2002, 67, 2778   DOI   ScienceOn
27 Jung, I. G.; Seo, J.; Lee, S. I.; Choi, S. Y.; Chung, Y. K. Organometallics 2006, 25, 4240   DOI   ScienceOn
28 Ikeda, S.-i.; Daimon, N.; Sanuki, R.; Odashima, K. Chem. Eur. J. 2006, 12, 1797   DOI   ScienceOn
29 Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635   DOI   ScienceOn
30 Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16   DOI
31 Delpech, F.; Asgatay, S.; Castel, A.; Rivière, P.; Rivière-Baudet, M.; Amin-Alami, A.; Manriquez, J. Appl. Organomet. Chem. 2001, 15, 626   DOI   ScienceOn
32 Hsu, C.-Y.; Orchin, M. J. Am. Chem. Soc. 1975, 97, 3553
33 Pittman, Jr. C. U.; Kawabata, Y.; Flowers, L. I. J. Chem. Soc., Chem. Commun. 1982, 473
34 Huddleston, R. R.; Krische, M. J. Synlett 2003, 12
35 Montgomery, J. Angew. Chem. Int. Ed. 2004, 43, 3890   DOI   ScienceOn
36 Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357   DOI   ScienceOn
37 Krische, M. J.; Jang, H.-Y. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier: Oxford, 2007; Vol 10, p 493
38 Widenhoefer, R. A.; Bender, C. F. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier: Oxford, 2007; Vol 11, p367
39 Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394   DOI   ScienceOn
40 Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809   DOI   ScienceOn
41 Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5334   DOI   ScienceOn
42 Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202   DOI   ScienceOn
43 Clark, H. C.; Kurosawa, H. Inorg. Chem. 1973, 12, 1566   DOI
44 Clark, H. C.; Jablonski, C. R.; Wong, C. S. Inorg. Chem. 1975, 14, 1332   DOI
45 Kurosawa, H. Inorg. Chem. 1976, 15, 120   DOI
46 Gómez, M.; Muller, G.; Salnz, D.; Sales, J. Organometallics 1991, 10, 4036   DOI
47 Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew. Chem. Int. Ed. 2004, 43, 711   DOI   ScienceOn
48 Nishiyama, H.; Shiomi, T.; Tsuchiya, Y.; Matsuda, I. J. Am. Chem. Soc. 2005, 127, 6972   DOI   ScienceOn
49 Miura, K.; Yamada, Y.; Tomita, M.; Hosomi, A. Synlett 2004, 1985
50 Freiría, M.; Whitehead, A. J.; Tocher, D. A.; Motherwell, W. B. Tetrahedron2004, 60, 2673   DOI   ScienceOn
51 Shiomi, T.; Ito, J.-I.; Yamamoto, Y.; Nishiyama, H. Eur. J. Org. Chem. 2006, 5594
52 Zhao, G.-L.; Cordova, A. Tetrahedron Lett. 2006, 47, 7417   DOI   ScienceOn
53 Lumby, R. J. R.; Joensuu, P. M.; Lam, H. W. Org. Lett. 2007, 9, 4367   DOI   ScienceOn
54 Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537   DOI   ScienceOn
55 Nishiyama, H.; Shiomi, T. Top Curr. Chem. 2007, 279, 105   DOI
56 Auber, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813   DOI   ScienceOn
57 Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 216
58 Widenhoefer, R. A. Acc. Chem. Res. 2002, 35, 905   DOI   ScienceOn
59 Ikeda, S.-I. Angew. Chem. Int. Ed. 2003, 42, 5120   DOI   ScienceOn
60 Lee, H.; Jang, M.-S.; Hong, J.-T.; Jang, H.-Y. Tetrahedron Lett. 2008, 49, 5785   DOI   ScienceOn
61 Zhao, C.-X.; Bass, J.; Morken, J. P. Org. Lett. 2001, 3, 2839   DOI   ScienceOn
62 Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923   DOI
63 Arime, T.; Kato, N.; Komadate, F.; Saegusa, H.; Mori, N. Synth. Commun. 1994, 24, 3315   DOI   ScienceOn
64 Zhao, C. X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829   DOI   ScienceOn
65 Baik, T.-G.; Luis, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112   DOI   ScienceOn
66 Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Lynch, V.; Schultz, A. J.; Wang, X.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448   DOI   ScienceOn
67 Jung, C. K.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 17051   DOI   ScienceOn
68 Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156   DOI   ScienceOn
69 Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653   DOI   ScienceOn
70 Jang, H.-Y.; Krische, M. J. Eur. J. Org. Chem. 2004, 19, 3953
71 Garner, S. A.; Krische, M. J. J. Org. Chem. 2007, 72, 5843   DOI   ScienceOn
72 Bee, C.; Han, S. B.; Hassan, A.; Iida, H.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 2746   DOI   ScienceOn