Iron nanoparticles catalyzing the asymmetric transfer hydrogenation of ketones

Journal of the American Chemical Society

Volumn 134, Issue 13, 2012, Pages 5893-5899

  Sonnenberg, Jessica F ^a   Coombs, Neil ^a   Dube, Paul A ^b   Morris, Robert H ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; ACTIVE SPECIES; ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFER HYDROGENATION; EDX ANALYSIS; FUNCTIONALIZED; FUNCTIONALIZED POLYMERS; INDUCTION PERIODS; IRON NANOPARTICLES; KINETIC INVESTIGATIONS; MICROSCOPY IMAGING; NON-PRECIOUS METALS; OPERANDO; POLYMER-SUPPORTED; SQUID MAGNETOMETRY; TETRADENTATE LIGANDS; TRANSFER HYDROGENATIONS; XPS ANALYSIS; ZEROVALENT;

CATALYSIS; EXPERIMENTS; HYDROGENATION; KETONES;

METAL NANOPARTICLES;

IRON; IRON NANOPARTICLE; KETONE; NANOPARTICLE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENERGY DISPERSIVE X RAY SPECTROSCOPY; HYDROGENATION; MAGNETOMETRY; ROENTGEN SPECTROSCOPY; SCANNING TRANSMISSION ELECTRON MICROSCOPY; SUPERCONDUCTING QUANTUM INTERFERENCE DEVICE MAGNETOMETRY; X RAY PHOTOELECTRON SPECTROSCOPY;

CATALYSIS; COLLOIDS; HYDROGENATION; IRON; KETONES; METAL NANOPARTICLES; POLYMERS;

EID: 84859335223     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211658t     Document Type: Article

References (72)

1. Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103-151
2. Naud, F.; Spindler, F.; Rueggeberg, C. J.; Schmidt, A. T.; Blaser, H. U. Org. Process Res. Dev. 2007, 11, 519-523
3. Pugin, B.; Blaser, H. U. Top. Catal. 2010, 53, 953-962
4. Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393-406
5. Samec, J. S. M.; Bäckvall, J. E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237-248
6. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73
7. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008-2022
8. Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282-2291
9. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254
10. Nakazawa, H.; Itazaki, M. Top. Organomet. Chem. 2011, 33, 27-81
11. Junge, K.; Schroder, K.; Beller, M. Chem. Commun. 2011, 47, 4849-4859
12. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317-3321
13. Jothimony, K.; Vancheesan, S.; Kuriacose, J. C. J. Mol. Catal. 1985, 32, 11-16
14. Jothimony, K.; Vancheesan, S. J. Mol. Catal. 1989, 52, 301-304
15. Chen, J. S.; Chen, L. L.; Xing, Y.; Chen, G.; Shen, W. Y.; Dong, Z. R.; Li, Y. Y.; Gao, J. X. Acta Chim. Sin. (Huaxue Xuebao) 2004, 62, 1745-1750
16. Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Angew. Chem., Int. Ed. 2008, 47, 940-943
17. Sui-Seng, C.; Haque, F. N.; Hadzovic, A.; Pütz, A. M.; Reuss, V.; Meyer, N.; Lough, A. J.; Zimmer-De Iuliis, M.; Morris, R. H. Inorg. Chem. 2008, 48, 735-743
18. Mikhailine, A.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 1394-1395
19. Sues, P. E.; Lough, A. J.; Morris, R. H. Organometallics 2011, 30, 4418-4431
20. Lagaditis, P. O.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2011, 133, 9662-9665
21. Meyer, N.; Lough, A. J.; Morris, R. H. Chem.-Eur. J. 2009, 15, 5605-5610
22. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317-341
23. Crabtree, R. H. Chem. Rev. 2012, 112, 1536 - 1554.
24. Henrici-Olivé, G.; Olivé, S. Angew. Chem., Int. Ed. 1976, 15, 136-141
25. Tasfy, S. F. H.; Zabidi, N. A. M.; Subbarao, D. J. Mater. Sci. Eng. A 2011, 1, 9-15
26. Schlögl, R. Angew. Chem., Int. Ed. 2003, 42, 2004-2008
27. Phua, P. H.; Lefort, L.; Boogers, J. A. F.; Tristany, M.; de Vries, J. G. Chem. Commun. 2009, 3747-3749
28. Rangheard, C.; de Julian Fernandez, C.; Phua, P. H.; Hoorn, J.; Lefort, L.; de Vries, J. G. Dalton Trans. 2010, 39, 8464-8471
29. Stein, M.; Wieland, J.; Steurer, P.; Toelle, F.; Muelhaupt, R.; Breit, B. Adv. Synth. Catal. 2011, 353, 523-527
30. Li, W. Z.; Xie, S. S.; Qian, L. X.; Chang, B. H.; Zou, B. S.; Zhou, W. Y.; Zhao, R. A.; Wang, G. Science 1996, 274, 1701-1703
31. Rizk, S.; Assouar, B. M.; De, P. L.; Alnot, P.; Bougdira, J. J. Phys. Chem. C 2009, 113, 8718-8723
32. Ruemmeli, M. H.; Schaeffel, F.; Kramberger, C.; Gemming, T.; Bachmatiuk, A.; Kalenczuk, R. J.; Rellinghaus, B.; Buechner, B.; Pichler, T. J. Am. Chem. Soc. 2007, 129, 15772-15773
33. Seah, C.-M.; Chai, S.-P.; Ichikawa, S.; Mohamed, A. R. Carbon 2012, 50, 960-967
34. Nguyen, D. D.; Tai, N.-H.; Chen, S.-Y.; Chueh, Y.-L. Nanoscale 2012, 4, 632-638
35. Comba, F. N.; Rubianes, M. D.; Herrasti, P.; Rivas, G. A. Sens. Actuators, B 2010, B149, 306-309
36. He, C.; Tian, G.; Liu, Z.; Feng, S. Org. Lett. 2010, 12, 649-651
37. Yan, J.-M.; Zhang, X.-B.; Han, S.; Shioyama, H.; Xu, Q. Angew. Chem., Int. Ed. 2008, 47, 2287-2289
38. Ban, Z.; Barnakov, Y. A.; Li, F.; Golub, V. O.; OConnor, C. J. J. Mater. Chem. 2005, 15, 4660-4662
39. Ranganath, K. V. S.; Kloesges, J.; Schäfer, A. H.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7786-7789
40. Costa, N. J. S.; Kiyohara, P. K.; Monteiro, A. L.; Coppel, Y.; Philippot, K.; Rossi, L. M. J. Catal. 2010, 276, 382-389
41. Prokopchuk, D. E.; Sonnenberg, J. F.; Meyer, N.; Iuliis, M. Z.-D.; Lough, A. J.; Morris, R. H. Accepted.
42. Lin, Y.; Finke, R. G. Inorg. Chem. 1994, 33, 4891-4910
43. Ranganath, K. V. S.; Glorius, F. Catal. Sci. Technol. 2011, 1, 13-22
44. Besson, C.; Finney, E. E.; Finke, R. G. J. Am. Chem. Soc. 2005, 127, 8179-8184
45. Clark, T. J.; Jaska, C. A.; Turak, A.; Lough, A. J.; Lu, Z. H.; Manners, I. Inorg. Chem. 2007, 46, 7394-7402
46. Cho, W. K.; Lee, J. K.; Kang, S. M.; Chi, Y. S.; Lee, H. S.; Choi, I. S. Chem.-Eur. J. 2007, 13, 6351-6358
47. Buil, M. L.; Esteruelas, M. A.; Niembro, S.; Oliván, M.; Orzechowski, L.; Pelayo, C.; Vallribera, A. Organometallics 2010, 29, 4375-4383
48. Mori, K.; Kondo, Y.; Yamashita, H. Phys. Chem. Chem. Phys. 2009, 11, 8949-8954
49. Hu, A.; Yee, G. T.; Lin, W. J. Am. Chem. Soc. 2005, 127, 12486-12487
50. Panella, B.; Vargas, A.; Baiker, A. J. Catal. 2009, 261, 88-93
51. Jansat, S.; Gómez, M.; Philippot, K.; Muller, G.; Guiu, E.; Claver, C.; Castillón, S.; Chaudret, B. J. Am. Chem. Soc. 2004, 126, 1592-1593
52. Alonso, F.; Riente, P.; Yus, M. Acc. Chem. Res. 2011, 44, 379-391
53. Lihl, F. Z. Metallkd. 1953, 44, 160
54. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424-9434
55. Bayram, E.; Linehan, J. C.; Fulton, J. L.; Roberts, J. A. S.; Szymczak, N. K.; Smurthwaite, T. D.; Özkar, S.; Balasubramanian, M.; Finke, R. G. J. Am. Chem. Soc. 2011, 133, 18889-18902
56. Lagaditis, P. O.; Lough, A. J.; Morris, R. H. Inorg. Chem. 2010, 49, 10057-10066
57. Hornstein, B. J.; Aiken, J. D.; Finke, R. G. Inorg. Chem. 2002, 41, 1625-1638
58. Tolman, C. A. Chem. Rev. 1977, 77, 313-348
59. Grosvenor, A. P.; Kobe, B. A.; Biesinger, M. C.; McIntyre, N. S. Surf. Interface Anal. 2004, 36, 1564-1574
60. Wagner, C. D.; Naumkin, A. V.; Kraut-Vass, A.; Allison, J. W.; Powell, C. J.; John, R.; Rumble, J. In NIST Standard Reference Database 20; U.S. Department of Commerce: 2003; Vol. Version 3.5.
61. Skomski, R. J. Phys.: Condens. Matter 2003, 15, R841-R896
62. Witham, C. A.; Huang, W.; Tsung, C.-K.; Kuhn, J. N.; Somorjai, G. A.; Toste, F. D. Nat. Chem 2010, 2, 36-41
63. Campbell, E. J.; Zhou, H.; Nguyen, S. T. Org. Lett. 2001, 3, 2391-2393
64. Santini, R.; Griffith, M. C.; Qi, M. Tetrahedron Lett. 1998, 39, 8951-8954
65. Banfi, L.; Narisano, E.; Riva, R. In e-EROS Encyclopedia of Reagents for Organic Synthesis; Wiley: 2001.
66. Alfons, B. J. Mol. Catal. A: Chem. 1997, 115, 473-493
67. Demers-Carpentier, V.; Goubert, G.; Masini, F.; Lafleur-Lambert, R.; Dong, Y.; Lavoie, S.; Mahieu, G.; Boukouvalas, J.; Gao, H.; Rasmussen, A. M. H.; Ferrighi, L.; Pan, Y.; Hammer, B.; McBreen, P. H. Science 2011, 334, 776-780
68. Wang, C. M.; Baer, D. R.; Amonette, J. E.; Engelhard, M. H.; Qiang, Y.; Antony, J. Nanotechnology 2007, 18, 255603
69. Bedford, R. B.; Betham, M.; Bruce, D. W.; Davis, S. A.; Frost, R. M.; Hird, M. Chem. Commun. 2006, 1398-1400
70. Hoch, L. B.; Mack, E. J.; Hydutsky, B. W.; Hershman, J. M.; Skluzacek, J. M.; Mallouk, T. E. Environ. Sci. Technol. 2008, 42, 2600-2605
71. Kavaliunas, A. V.; Taylor, A.; Rieke, R. D. Organometallics 1983, 2, 377-383
72. Kyriakou, G.; Beaumont, S. K.; Lambert, R. M. Langmuir 2011, 27, 9687-9695