An in situ generated samarium complex as a practical catalyst for the efficient intramolecular hydroamination of non-activated alkenes

Tetrahedron Letters

Volumn 49, Issue 34, 2008, Pages 5032-5035

  Quinet, Coralie ^a   Ates, Ali ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; SAMARIUM;

AMINATION; ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; CYCLIZATION; PROTON TRANSPORT; SUBSTITUTION REACTION;

EID: 46749120916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.053     Document Type: Article

References (55)

1. Smith P.A.S. The Chemistry of Open-Chain Organic Nitrogen Compounds (1965), Benjamin W.A.
2. Patai S. The Chemistry of The Functional Groups, The Chemistry of The Amino Group (1968), Interscience
3. Brown B.R. The Organic Chemistry of Aliphatic Nitrogen Compounds (1994), Oxford (University Press), England
4. Seayad J., Tillack A., Hartung C.G., and Beller M. Adv. Synth. Catal. 344 (2002) 795
5. For general references on hydroamination, see:. Gasc M.B., Lattes A., and Perie J.J. Tetrahedron 39 (1983) 703
6. Steinborn D., Brunet J.-J., Neibecker D., and Niedercorn F. J. Mol. Catal. 49 (1989) 235
7. Roundhill D.M. Chem. Rev. 92 (1992) 1
8. Müller T.E., and Beller M. Chem. Rev. 98 (1998) 675
9. Brunet J.-J., and Neibecker D. In: Togni A., and Grützmacher H. (Eds). Catalytic Heterofunctionalization (2001), Wiley-VCH 91 Chapter 4
10. See Ref. 1.
11. Molander G.A., and Romero J.A.C. Chem. Rev. 102 (2002) 2161
12. Pohlki F., and Doye S. Chem. Soc. Rev. 32 (2003) 104
13. Hartwig J.F. Pure Appl. Chem. 76 (2004) 507
14. Hong S., and Marks T.J. Acc. Chem. Res. 37 (2004) 673
15. Ates A., and Quinet C. Eur. J. Org. Chem. (2003) 1623
16. Quinet C., Jourdain P., Hermans C., Ates A., Lucas I., and Markó I.E. Tetrahedron 64 (2008) 1077
17. For hydroamination of alkenes mediated by transition metals, see:. Stern E.W., and Spector M.L. Proc. Chem. Soc. London (1961) 370
18. Coulson D.R. Tetrahedron Lett. (1971) 429
19. Akermark B., Bäckvall J.E., Hegedus L.S., Zetterberg K., Siirala-Hansen K., and Sjöberg K. J. Organomet. Chem. 72 (1974) 127
20. Gasc M.B., Lattes A., and Perie J.J. Tetrahedron 34 (1978) 1943
21. 2a.
22. Brunet J.-J., Neibecker D., and Philippot K. Tetrahedron Lett. 34 (1993) 3877
23. See, for example:. Gribkov D.V., and Hultzsch K.C. Angew. Chem., Int. Ed. 43 (2004) 5542
24. Kim J.Y., and Livinghouse T. Org. Lett. 7 (2005) 4391
25. Bender C.F., and Widenhoefer R.A. J. Am. Chem. Soc. 127 (2005) 1070
26. Han X., and Widenhoefer R.A. Angew. Chem., Int. Ed. 45 (2006) 1747
27. Bexrud J.A., Beard J.D., Leitch D.C., and Schafer L.L. Org. Lett. 7 (2005) 1959
28. Michael F.E., and Cochran B.M. J. Am. Chem. Soc. 128 (2006) 4246
29. Zhang J., Yang C.-G., and He C. J. Am. Chem. Soc. 128 (2006) 1798
30. Müller C., Loos C., Schulenberg N., and Doye S. Eur. J. Org. Chem. (2006) 2499
31. Johns A.M., Utsunomiya M., Incarvito C.D., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 1828
32. For selected references on lanthanide and actinide-catalysed hydroaminations, see: With metallocene Ln catalysts:. Gagné M.R., Nolan S.P., and Marks T.J. Organometallics 9 (1990) 1716
33. Molander G.A., and Dowdy E.D. J. Org. Chem. 63 (1998) 8983
34. Ryu J.-S., Li G.Y., and Marks T.J. J. Am. Chem. Soc. 125 (2003) 12584
35. Molander G.A., and Pack S.K. J. Org. Chem. 68 (2003) 9214
36. Stubbert B.D., and Marks T.J. J. Am. Chem. Soc. 129 (2007) 4253
37. With biphenolate and binaphtholate Ln catalysts:. Gribkov D.V., Hultzsch K.C., and Hampel F. J. Am. Chem. Soc. 128 (2006) 3748
38. Yu X., and Marks T.J. Organometallics 26 (2007) 365
39. With diamine/diamide Ln catalysts:. Kim Y.K., Livinghouse T., and Bercaw J.E. Tetrahedron Lett. 42 (2001) 2933
40. Kim Y.K., and Livinghouse T. Angew. Chem., Int. Ed. 41 (2002) 3645
41. Roesky P.W., and Muller T.E. Angew. Chem., Int. Ed. 42 (2003) 2708
42. Hultzsch K.C., Hampel F., and Wagner T. Organometallics 23 (2004) 2601
43. Kim Y.K., and Livinghouse T. Org. Lett. 7 (2005) 1737
44. Riegert D., Collin J., Meddour A., Schultz E., and Trifonov A. J. Org. Chem. 71 (2006) 2514
45. Rastätter M., Zulys A., and Roesky P.W. Chem. Eur. J. 13 (2007) 3606
46. Gagné M.R., and Marks T.J. J. Am. Chem. Soc. 111 (1989) 4108
47. Gagné M.R., Stern C.L., and Marks T.J. J. Am. Chem. Soc. 114 (1992) 275
48. Motta A., Lanza G., Fragala' I.L., and Marks T.J. Organometallics 23 (2004) 4097
49. Motta A., Fragala' I.L., and Marks T.J. Organometallics 25 (2006) 5533
50. It is interesting to note that the presence of a hydrogen atom on the nitrogen of complex 13 appears to play a crucial role in the success of these hydroamination reactions. Indeed, attempted cyclisation of the secondary aminoolefin 16, under the optimal conditions developed for the primary amines, did not yield the corresponding piperidine adduct, even after 20 h.{A figure is presented}
51. Bürgstein M.R., Berberich H., and Roesky P.W. Chem. Eur. J. 7 (2001) 3078
52. Hultzsch K.C., Gribkov D.V., and Hampel F. J. Organomet. Chem. (2005) 4441
53. In some experiments using the first-generation catalytic system, a characteristic colour change of the mixture (from blue to yellow) was occasionally observed without detrimental effect on the efficiency of the reaction.
54. 2 was added, followed by the aminoolefin. Using this protocol, results similar to those obtained under conditions (b) could be achieved after 24 h at 100 °C.
55. -1): 3391 [s], 2957-2866 [s], 1649- 1560 [s], 1456-1381 [m], 1356 [m], 1090 [w], 1036 [w], 800 [w], 702 [w]. CAS: [19451-50-4] cis-(S,S).