Polymer-incarcerated chiral Rh/Ag nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: Remarkable effects of bimetallic structure on activity and metal leaching

Journal of the American Chemical Society

Volumn 134, Issue 41, 2012, Pages 16963-16966

  Yasukawa, Tomohiro ^a   Miyamura, Hiroyuki ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-ADDITION; AEROBIC OXIDATIONS; ALLYL ALCOHOLS; ARYLBORONIC ACIDS; BIMETALLIC STRUCTURES; CHIRAL LIGAND; HIGH YIELD; METAL LEACHING; ONE POT; SIMPLE OPERATION;

ADDITION REACTIONS; CATALYSTS; LEACHING; RHODIUM;

METAL NANOPARTICLES;

ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; GOLD NANOPARTICLE; POLYMER; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OXIDATION;

ALDEHYDES; BORONIC ACIDS; KETONES; METAL NANOPARTICLES; MOLECULAR STRUCTURE; POLYMERS; RHODIUM; SILVER;

EID: 84867535651     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307913e     Document Type: Article

References (60)

1. Metal Nanoclusters in Catalysis and Materials Science: The Issue of Size Control; Corain, B., Schmid, G., Toshima, N., Eds.; Elsevier: Amsterdam, 2007.
2. Feldheim, D. L.; Foss, C. A. Metal Nanoparticles: Synthesis, Characterization, and Applications; CRC Press: Boca Raton, FL, 2001.
3. Kobayashi, S.; Miyamura, H. Chem. Rec. 2010, 10, 271
4. Yan, N.; Xiao, C.; Kou, Y. Coord. Chem. Rev. 2010, 254, 1179
5. Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc 2011, 133, 3095
6. Wang, N.; Matsumoto, T.; Ueno, M.; Miyamura, H.; Kobayashi, S. Angew. Chem., Int. Ed. 2009, 48, 4744
7. Munoz-Flores, B. M.; Kharisov, B. I.; Jimenez-Perez, V. M.; Martinez, P. E.; Lopez, S. T. Ind. Eng. Chem. Res. 2011, 50, 7705
8. Ferrando, R.; Jellinek, J.; Johnston, R. L. Chem. Rev. 2008, 108, 845
9. Liu, P.; Nørskov, J. K. Phys. Chem. Chem. Phys. 2001, 3, 3814
10. Toshima, N.; Yonezawa, T. New J. Chem. 1998, 22, 1179
11. Cong, H.; Porco, J. A. ACS Catal. 2012, 2, 65
12. Witham, C. A.; Huang, W.; Tsung, C.-K.; Kuhn, J. N.; Somorjai, G. A.; Toste, F. D. Nat. Chem. 2010, 2, 36
13. Ranganath, K. V. S.; Kloesges, J.; Schäfer, A. H.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7786
14. Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco, J. A. J. Am. Chem. Soc 2010, 132, 7514
15. Mori, K.; Kondo, Y.; Yamashita, H. Phys. Chem. Chem. Phys. 2009, 11, 8949
16. Sawai, K.; Tatumi, R.; Nakahodo, T.; Fujihara, H. Angew. Chem., Int. Ed. 2008, 47, 6917
17. Abad, A.; Corma, A.; Garcia, H. Top. Catal. 2007, 44, 237
18. Park, K. H.; Chung, Y. K. Adv. Synth. Catal. 2005, 347, 854
19. Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 3469
20. Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95
21. Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. Synlett 2011, 1345
22. Hargrave, J. D.; Allen, J. C.; Frost, C. G. Chem.-Asian J. 2010, 5, 386
23. Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093
24. Youn, S. W. Eur. J. Org. Chem. 2009, 2597
25. Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535
26. Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482
27. Paquin, J.-F.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc 2005, 127, 10850
28. Guo, H. C.; Ma, J. A. Angew. Chem., Int. Ed. 2006, 45, 354
29. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
30. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579
31. Howell, G. P. Org. Process Res. Dev. 2012, 16, 1258
32. Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
33. Brock, S.; Hose, D.; Moseley, J.; Parker, A.; Patel, I.; Williams, A. Org. Process Res. Dev. 2008, 12, 496
34. Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Green Chem. 2012, 14, 338
35. Jana, R.; Tunge, J. A. J. Org. Chem. 2011, 76, 8376
36. Jana, R.; Tunge, J. A. Org. Lett. 2009, 11, 971
37. Laska, U.; Frost, C. G.; Plucinski, P. K.; Price, G. J. Catal. Lett. 2007, 122, 68
38. Otomaru, Y.; Senda, T.; Hayashi, T. Org. Lett. 2004, 6, 3357
39. Uozumi, Y.; Nakazono, M. Adv. Synth. Catal. 2002, 344, 274
40. Guerreiro, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423
41. Motokura, K.; Hashimoto, N.; Hara, T.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Green Chem. 2011, 13, 2416
42. Neatu, F.; Besnea, M.; Komvokis, V. G.; Genet, J. P.; Michelet, V.; Triantafyllidis, K. S.; Parvuescu, V. I. Catal. Today 2008, 139, 161
43. Laska, U.; Frost, C. G.; Plucinski, P. K.; Price, G. J. Catal. Lett. 2008, 122, 68
44. Kantam, M. L.; Subrahmanyam, V. B.; Kumar, K. B. S.; Venkanna, G. T.; Sreedhar, B. Helv. Chim. Acta 2008, 91, 1947
45. Handa, P.; Witula, T.; Reis, P.; Holmberg, K. ARKIVOC 2008, vi) 107
46. Handa, P.; Holmberg, K.; Sauthier, M.; Castanet, Y.; Mortreux, A. Microporous Mesoporous Mater. 2008, 116, 424
47. Fujita, N.; Motokura, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Jitsukawa, K.; Kaneda, K. Tetrahedron Lett. 2006, 47, 5083
48. Akiyama, R.; Kobayashi, S. Chem. Rev. 2009, 109, 594
49. Kaizuka, K.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc 2010, 132, 15096
50. Miyamura, H.; Matsubara, R.; Kobayashi, S. Chem. Commun. 2008, 2031
51. Yuan, Y.; Yan, N.; Dyson, P. J. ACS Catal. 2012, 2, 1057
52. Guyonnet-Bilé, E.; Denicourt-Nowicki, A.; Sassine, R.; Beaunier, P.; Launay, F.; Roucoux, A. ChemSusChem 2010, 3, 1276
53. Han, D.; Li, X.; Zhang, H.; Liu, Z.; Li, J.; Li, C. J. Catal. 2006, 243, 318
54. Bile, E. G.; Cortelazzo-Polisini, E.; Denicourt-Nowicki, A.; Sassine, R.; Launay, F.; Roucoux, A. ChemSusChem 2012, 5, 91
55. Crabtree, R. H. Chem. Rev. 2012, 112, 1536
56. Heitbaum, M.; Glorius, F.; Escher, I. Angew. Chem., Int. Ed. 2006, 45, 4732
57. Lucchesi, C.; Inasaki, T.; Miyamura, H.; Matsubara, R.; Kobayashi, S. Adv. Synth. Catal. 2008, 350, 1996
58. Okamoto, K.; Hayashi, T.; Rawal, V. H. Chem. Commun. 2009, 4815
59. Okamoto, K.; Hayashi, T.; Rawal, V. H. Org. Lett. 2008, 10, 4387
60. Miyamura, H.; Matsubara, R.; Miyazaki, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 4151