Hydroaminomethylation with novel Rhodium-Carbene complexes: An efficient catalytic approach to pharmaceuticals

Chemistry - A European Journal

Volumn 13, Issue 5, 2007, Pages 1594-1601

  Ahmed, Moballigh ^a   Buch, Cathleen ^a   Routaboul, Lucie ^a   Jackstell, Ralf ^a   Klein, Holger ^a   Spannenberg, Anke ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amines; Carbenes; Carbonylation; Hydroaminomethylation; Pharmaceuticals; Rhodium

Indexed keywords

CATALYST ACTIVITY; CATALYSTS; COMPLEXATION; DRUG PRODUCTS; REGIOSELECTIVITY; RHODIUM; SYNTHESIS (CHEMICAL);

HYDROAMINOMETHYLATION; MODEL SYSTEM;

AMINES;

1,1 DIPHENYLETHYLENE; 1,1-DIPHENYLETHYLENE; ALKENE; AMINE; CARBENE; DRUG; DRUG DERIVATIVE; HYDROCARBON; IMIDAZOLE DERIVATIVE; LIGAND; METHANE; ORGANOMETALLIC COMPOUND; PIPERIDINE; PIPERIDINE DERIVATIVE; PROPANE; RHODIUM; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; SYNTHESIS;

ALKENES; AMINES; CATALYSIS; HYDROCARBONS; IMIDAZOLES; LIGANDS; METHANE; METHYLATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHARMACEUTICAL PREPARATIONS; PIPERIDINES; PROPANE; RHODIUM; STYRENES;

EID: 34250372456     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601155     Document Type: Article

References (59)

1. a) Reviews: P. Eilbracht, L. Bärfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck, A. Schmidt, Chem. Rev. 1999, 99, 3329-3365;
2. b) F. Ungvary, Coord. Chem. Rev. 2004, 248, 867-880.
3. a) L. Routaboul, C. Buch, H. Klein, R. Jackstell, M. Beller, Tetrahedron Lett. 2005, 46, 7401-7405;
4. b) I. D. Kostas, J. Chem. Res. Synop. 1999, 630-631;
5. c) Y.-S. Lin, B. El Ali, H. Alper, Tetrahedron Lett. 2001, 42, 2423-2425.
6. a) A. Kleemann, J. Engel, Pharmazeutische Wirkstoffe, Thieme, Stuttgart. 1987;
7. b) H. Certa, G. Blaschke, Arch. Pharm. 1990, 323, 744-747;
8. c) H. M. Piper, J. F. Hütler, P. G. Spieckermann, Anneim.-Forsch. 1985, 35, 1495-1498.
9. a) N. Burrows, J. G. Cumming, S. M. Fillery, G. A. Hamlin, J. A. Hudson, R. J. Jackson, S. McLaughlin, J. S. Shaw, Bioorg. Med. Chem. 2005, 13, 25-28;
10. b) R. R. Goehring, J. F. W. Whitehead, K. Brown, K. Islam, X. Wen, X. Zhou, Z. Chen, K. J. Valenzano, W. S. Miller, S. Shan, D. J. Kyle, Bioorg. Med. Chem. 2004, 12, 5045-5050;
11. c) Z. Chen, W. S. Miller, S. Shan, K. J. Valenzano, Bioorg. Med. Chem. 2003, 11, 3247-3252.
12. C. Botteghi, G. Chelucci, G. Del Pontc, M. Marchetti, S. Paganelli, J. Org. Chem. 1994, 59, 7125-7127.
13. M. Marchetti, B. Sechi, C. Botteghi, S. Paganelli, Bollettino Chimico Farmaceutico 1998, 137, 74-76.
14. T. Rische, P. Eilbracht, Tetrahedron 1999, 55, 1915-1920.
15. M. Ahmed, A. M. Seayad, R. Jackstell, M. Beller, J. Am. Chem. Soc. 2003, 125, 10311-10318.
16. C. Butteghi, L. Cazzolato, M. Marchetti, S. Paganelli, J. Org. Chem. 1995, 60, 6612-6615.
17. K. Öfele, J. Organomet. Chem. 1968, 12, P42.
18. W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363;
19. Angew. Chem. Int. Ed. 2002, 41, 1290-1309.
20. For recent applications see; a) A. Leleu, Y. Fort, R. Schneider, Adv. Synth. Catal. 2006, 348, 1086-1092;
21. b) C. Yan, X. Zeng, W. Zhang, M. Luo, J. Organomet. Chem. 2006, 691, 3391-3396;
22. c) N. Ajellal, C. M. Thomas, J.-F. Carpentier, Adv. Synth. Catal. 2006, 348, 1093-1100;
23. d) S. Nanchen, A. Pfaltz, Chem. Eur. J. 2006, 12, 4550-4558;
24. e) W. A. Herrmann, K. Öfele, S. K. Schneider, E. Herdtweck, S. D. Hoffmann, Angew. Chem. 2006, 118, 3943-3947;
25. Angew. Chem. Int. Ed. 2006, 45, 3859-3862;
26. f) M. M. Rogers, J. E. Wendlandt, I. A. Guzei, S. S. Stahl, Org. Lett. 2006, 8, 2257-2260;
27. g) M. Bortenschlager, J. Schuetz, D. Von Preysing, O. Nuyken, W. A. Herrmann, R. Weberskirch, J. Organomet. Chem. 2005, 690, 6233-6237;
28. h) M. F. Lappert, J. Organomet. Chem. 2005, 690, 5467-5473.
29. W. A. Herrmann, J. Fischer, M. Elison, C. Köcher, (Hoechst AG), DE4447068.1 A1, 1994; EP 0719758 A1; US 5703269, 1997
30. [Chem. Abstr. 1996, 125, 167571y].
31. A. C. Chen, L. Ren, A. Decken, C. M. Crudden, Organometallics 2000, 19, 3459.
32. M. Poyatos, P. Uriz, J. A. Mata, E. Fernandez, E. Peris, C. Claver, Organometullics 2003, 22, 440-444.
33. K. Weigl, K. Köhler, S. Dechert, F. Meyer, Organometallics 2005, 24, 4049-4056.
34. a) R. Jackstell, M. Gomez, A. Frisch, H. Klein, K. Selvakumar, A. Zapf, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028-1031;
35. Angew. Chem. Int. Ed. 2002, 41, 986-989;
36. b) K. Selvakumar, A. Zapf, A. Spannenberg, M. Beller, Chem. Eur. J. 2002, 8, 3901-3906.
37. a) A. C. Chen, D. P. Allen, C. M. Crudden, R. Wang, A. Decken, Can. J. Chem. 2005, 83, 943-957;
38. b) M. S. Datt, J. J. Nair, S. Otto, J. Organomet. Chem. 2005, 690, 3422-3426;
39. c) E. Fooladi, B. Dalhus, M. Tilset, Dalton Trans. 2004, 3909-3917;
40. d) P. A. Evans, E. W. Baum, A. N. Fazal, M. Pink, Chem. Commun. 2005, 63-65;
41. e) T. A. Betley, J. C. Peters, Angew. Chem. 2003, 115, 2487-2491;
42. Angew. Chem. Int. Ed. 2003, 42, 2385-2389;
43. f) J. Huang, E. D. Stevens, S. P. Nolan, Organometallics 2000, 19, 1194;
44. g) G. A. Grasa, Z. Moore, K. L. Martin, E. D. Stevens, S. P. Nolan, V. Paquet, H. Lebel, J. Organomet. Chem. 2002, 658, 126-131;
45. h) H. Karabiyik, R. Kilincarslan, M. Aygun, B. Cetikaya, O. Buyukgungor, Z. Naturforsch. B: Chem. Sci. 2005, 837-842.
46. J. Evans, Chem. Commun. 2005, 63-65.
47. a) A. M. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, M. Beller, Science 2002, 297, 1676-1678;
48. b) A. M. Seayad, S. Kumaravel, M. Ahmed, M. Beller, Tetrahedron Lett. 2003, 44, 1679-1683;
49. c) M. Ahmed, A. M. Seayad, R. Jackstell, M. Beller, Angew. Chem. 2003, 115.;
50. Angew. Chem. Int. Ed. 2003, 42, 5773-5777;
51. d) M. Ahmed, R. Jackstell, A. M. Seayad, H. Klein, M. Beller, Tetrahedron Lett. 2004, 45, 869-873.
52. D. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. S. You, W. Baumann, Angew. Chem. 2002, 114, 814-817;
53. Angew. Chem. Int. Ed. 2002, 41, 777-780.
54. C. Botteghi, S. Paganelli, L. Bigini, M. Marchetti, J. Mol. Catal. 1994, 93, 279-287.
55. T. Mizoroki, M. Kioka, M. Suzuki, S. Sakatani, A. Okumura, K. Maruya, Bull. Chem. Soc. Jpn. 1984, 57, 577-578.
56. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, Butterworth, New York, 4th ed., 1997.
57. G. F. Hennion, C. C. Price, C. V. Wolff, Jr., J. Am. Chem. Soc. 1955, 77, 4633-4636.
58. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
59. G. M. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.