Copper-in-charcoal (Cu/C): Heterogeneous, copper-catalyzed asymmetric hydrosilylations

Angewandte Chemie - International Edition

Volumn 45, Issue 8, 2006, Pages 1259-1264

  Lipshutz, Bruce H ^a   Frieman, Bryan A ^a   Tomaso Jr , Anthony E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Asymmetric catalysis; Copper; Heterogeneous catalysis; Hydrosilylation

Indexed keywords

ALKYLATION; BUTENES; CATALYSIS; CHEMICAL ANALYSIS; COPPER COMPOUNDS; HYDRIDES; METHANE; MOLECULAR STRUCTURE; PHOSPHATES; SILANES;

ASYMMETRIC CATALYSIS; COPPER CHEMISTRY; HETEROGENEOUS; HYDROSILYLATIONS;

CHARCOAL;

EID: 33746198775     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503149     Document Type: Article

References (59)

1. H. U. Blaser, A. Baiker, R. Prins, Heterogeneous Catalysis and Fine Chemicals IV, Elsevier, Netherlands, 1997.
2. J. R. Anderson, Structure of Metallic Catalysts, Academic Press, New York, 1975;
3. E. Bekyarova, D. Mehandjiev, J. Colloid Interface Sci. 1996, 179, 509;
4. A. B. Stiles, Catalyst Supports and Supported Catalysts, Butterworth, Boston, 1987, chap. 5.
5. L. M. Gandia, M. Montes, J. Catal. 1994, 145, 276;
6. M. Domingo-Garcia, I. Fernández-Moráles, F. J. López-Garzón, Appl. Catal. A 1994, 112, 75.
7. A. R. Silva, J. L. Figueiredo, C. Freire, B. de Castro, Catal. Today 2005, 102-103, 154;
8. T. Tsoncheva, S. Vankova, O. Bozhkov, D. Mehandjiev, J. Mol. Catal. A 2005, 225, 245.
9. B. H. Lipshutz, S. Tasler, W. Chrisman, B. Spliethoff, B. Tesche, J. Org. Chem. 2003, 68, 1177.
10. S. I. Lee, S. U. Son, M. R. Choi, Y. K. Chung, S.-G. Lee, Tetrahedron Lett. 2003, 44, 4705;
11. S. U. Son, S. I. Lee, Y. K. Chung, Angew. Chem. 2000, 112, 4318;
12. Angew. Chem. Int. Ed. 2000, 39, 4158.
13. T. Tsoncheva, S. Vankova, D. Mehandjiev, Fuel 2003, 82, 755.
14. B. H. Lipshutz, B. A. Frieman, Angew. Chem. 2005, 117, 6503;
15. Angew. Chem. Int. Ed. 2005, 44, 6345.
16. A. J. Garrat-Reed, D. C. Bell, Energy Dispersive X-Ray Analysis in the Electron Microscope BIOS, Scientific Publishers, Oxfordshire, 2002;
17. M. Arif Hayat, Principles and Techniques of Scanning Electron Microscopy, Van Nostrand Reinhold, New York, 1975.
18. I. Kummerow, D. L. Trimm, M. S. Wainwright, Appl. Catal. 1986, 27, 161.
19. F. Zaccheria, N. Ravasio, R. Psaro, A. Fusi, Tetrahedron Lett. 2005, 46, 3695;
20. N. Ravasio, R. Psaro, F. Zaccheria, Tetrahedron Lett. 2002, 43, 3943;
21. N. , Ravasio, M. Antenori, M. Gargano, P. Mastrorilli, Tetrahedron Lett. 1996, 37, 3529;
22. N. Ravasio, M. Rossi, J. Org. Chem. 1991, 56, 4329.
23. Comprehensive Asymmetric Catalysis I-III (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
24. Asymmetric Catalysis in Organic Synthesis (Ed.: R. Noyori), Wiley, New York, 1994.
25. a) C. Bolm, J.-C. Frison, J. Le Paih, C. Moessner, G. Raabe, J. Organomet. Chem. 2004, 689, 3767;
26. b) A. P. Duncan, J. L. Leighton, Org. Lett. 2004, 6, 4117;
27. c) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
28. Angew. Chem. Int. Ed. 2002, 41, 1290, and references therein.
29. a) B. H. Lipshutz, K. Noson, W. Chrisman, A. Lower, J. Am. Chem. Soc. 2003, 125, 8779;
30. b) B. H. Lipshutz, J. M. Servesko, T. B. Petersen, P. P. Papa, A. Lover, Org. Lett. 2004, 6, 1273;
31. c) B. H. Lipshutz, H. Shimizu, Angew. Chem. 2004, 114, 2278;
32. Angew. Chem. Int. Ed. 2004, 43, 2228;
33. d) B. H. Lipshutz, J. M. Servesko, B. R. Taft, J. Am. Chem. Soc. 2004, 126, 8352;
34. e) B. H. Lipshutz, A. Lower, K. Noson, Org. Lett. 2002, 4, 4045.
35. R. Nickolov, T. Tsoncheva, D. Mehandjiev, Fuel 2001, 81, 203;
36. B. Park, S. Park, S. Ryu, J. Colloid Interface Sci. 1999, 217, 142;
37. for the preparation of copper-on-graphite, see: A. Fuerstner, F. Hofer, H. Weidmann, Carbon 1991, 29, 915;
38. B. H. Lipshutz, M. Koerner, D. A. Parker, Tetrahedron Lett. 1987, 28, 945.
39. J. Zhao, Z. Liu, D. Sun, J. Catal. 2004, 227, 297;
40. H. Tseng, M. Wey, Carbon 2004, 42, 2269.
41. B. H. Lipshutz, S. Tasler, Adv. Synth. Catal. 2001, 343, 327.
42. While PMHS purchased from Lancaster and used as received works well in this chemistry, the material from Acros was surprisingly ineffective as a source of hydride.
43. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264.
44. Available from Solvias, Inc.; cf. H.-U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Studer, A. Togni, Top. Catal. 2002, 19, 3.
45. R. Schmid, E. A. Broger, M. Cereghetti, Y. Crameri, J. Foricher, M. Lalonde, R. K. Muller, M. Scalone, G. Schoettel, U. Zutter, Pure Appl. Chem. 1996, 68, 131;
46. R. Schmid, J. Foricher, M. Ceregetti, P. Schonholzer, Helv. Chim. Acta 1991, 74, 370.
47. T. Ohkuma, M. Kitamura, R. Noyori, Asymmetric Hydrogenation. Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, chap. 1, and references therein.
48. B. H. Lipshutz, J. M. Servesko, Angew. Chem. 2003, 115, 4937;
49. Angew. Chem. Int. Ed. 2003, 42, 4789.
50. B. H. Lipshutz, B. A. Frieman, J. B. Unger, D. M. Nihan, Can. J. Chem. 2005, 83, 606.
51. G. Hughes, M. Kimura, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11253.
52. Quantitative determination of the extent of ligand retention has yet to be determined.
53. A. W. Varnes, Handbook of Instrumental Techniques for Analytical Chemistry (Ed.: F. Settle), Prentice Hall, Upper Saddle River, NJ, 1997, p. 395.
54. 4OH; pH 10) led to no visible sign of copper in solution;
55. b) B. H. Lipshutz, Organometallics in Synthesis: A Manual, 2nd ed. (Ed.: M. Schlosser), Wiley, Chichester, 2002, chap. 6, and references therein;
56. Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, New York, 2002;
57. B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135.
58. B. Fultz, J. M. Howe, Transmission Electron Microscopy and Diffractometry of Materials, Springer, New York, 2002.
59. 0/C.