Tetrabenzyltitanium: An improved catalyst for the activation of sp 3 C-H bonds adjacent to nitrogen atoms

ChemCatChem

Volumn 1, Issue 1, 2009, Pages 162-172

  Prochnow, Insa ^a   Kubiak, Raphael ^a   Frey, Okko N ^a   Beckhaus, Rüdiger ^a   Doye, Sven ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

Alkenes; Amines; C H activation; Homogeneous catalysis; Titanium

Indexed keywords

C-H ACTIVATION; CYCLIZATIONS; HOMOGENEOUS CATALYSIS; INTERMOLECULAR REACTIONS; METAL-CATALYZED; NITROGEN ATOM; POOR EFFICIENCIES; TITANIUM-BASED;

ACTIVATION ANALYSIS; AMINES; HYDROCARBONS; NITROGEN; OLEFINS; REACTION KINETICS; STYRENE; TITANIUM;

CATALYSTS;

EID: 70350034841     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.200900092     Document Type: Article

References (70)

1. For reviews on catalytic C-H activation, see: a) F. Kakiuchi, S. Murai in Activation of Unreactive Bonds and Organic Synthesis (Ed: S. Murai), Springer, Berlin, 1999, pp. 47-79;
2. b) S.-I. Murahashi, H. Takaya, Acc. Chem. Res. 2000, 33, 225-233;
3. c) Handbook of C-H Transformations (Ed: G. Dyker), Wiley-VCH, Weinheim, 2005;
4. d) A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439-2463;
5. e) M. Tobisu, N. Chatani, Angew. Chem. 2006, 118, 1713-1715;
6. Angew. Chem. Int. Ed. 2006, 45, 1683-1684;
7. f) J.-Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041-4047;
8. g) R. G. Bergman, Nature 2007, 446, 391-393.
9. For reviews on catalytic C-H activation in the a-position to a nitrogen atom, see: a) K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069-1084;
10. b) S. Doye, Angew. Chem. 2001, 113, 3455-3457;
11. Angew. Chem. Int. Ed. 2001, 40, 3351-3353.
12. For selected examples of catalytic C-H activation in the a-position to a nitrogen atom, see: a) C.-H. Jun, D.-C. Hwang, S.-J. Na, Chem. Commun. 1998, 1405-1406;
13. b) N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882-12883;
14. c) S.-I. Murahashi, N. Komiya, H. Teraki, Angew. Chem. 2005, 117, 7091-7093;
15. Angew. Chem. Int. Ed. 2005, 44, 6931-6933;
16. d) S. J. Pastine, D. V. Gribkov, D. Sames, J. Am. Chem. Soc. 2006, 128, 14220-14221;
17. e) N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882-12883;
18. f) A. J. Catino, J. M. Nichols, B. J. Nettles, M. P. Doyle, J. Am. Chem. Soc. 2006, 128, 5648-5649;
19. g) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968-6969;
20. h) O. Baslé, C. J. Li, Org. Lett. 2008, 10, 3661-3663;
21. i) S. Sakaguchi, T. Kubo, Y. Ishii, Angew. Chem. 2001, 113, 2602-2604;
22. Angew. Chem. Int. Ed. 2001, 40, 2534-2536;
23. j) S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180-12181;
24. k) Z. Li, R. Yu, H. Li, Angew. Chem. 2008, 120, 7607-7610;
25. Angew. Chem. Int. Ed. 2008, 47, 7497-7500.
26. a) S. B. Herzon, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 6690-6691;
27. b) S. B. Herzon, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 14940-14941.
28. For reviews on hydroamination reactions, see: a) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
29. b) E. Haak, S. Doye, Chem. Unserer Zeit 1999, 33, 296-303;
30. c) J. J. Brunet, D. Neibecker in Catalytic Hetero-functionalization (Eds: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, pp. 91-141;
31. d) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114;
32. e) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935-946;
33. f) P. W. Roesky, T. E. Müller, Angew. Chem. 2003, 115, 2812-2814;
34. Angew. Chem. Int. Ed. 2003, 42, 2708-2710;
35. g) S. Doye, Synlett 2004, 1653-1672;
36. h) F. Alonso, I. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3160;
37. i) K. C. Hultzsch, Adv. Synth. Catal. 2005, 347, 367-391;
38. j) A. Odom, Dalton Trans. 2005, 225-233;
39. k) K. C. Hultzsch, Org. Biomol. Chem. 2005, 3, 1819-1824;
40. l) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555-4563;
41. m) J.-J. Brunet, N.-C. Chu, M. Rodriguez-Zubiri, Eur. J. Inorg. Chem. 2007, 4711-4722;
42. n) I. Aillaud, J. Collin, J. Hannedouche, E. Schulz, Dalton Trans. 2007, 5105-5118;
43. o) A. V. Lee, L. L. Schafer, Eur. J. Inorg. Chem. 2007, 2243-2255;
44. p) J.-J. Brunet, N.-C. Chu, M. Rodriguez-Zubiri, Eur. J. Inorg. Chem. 2007, 4711-4722;
45. q) R. Severin, S. Doye, Chem. Soc. Rev. 2007, 36, 1407-1420;
46. r) T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892;
47. s) S. Doye in Science of Synthesis, Vol. 40a, Georg Thieme Verlag KG, Stuttgart, 2009, pp. 241-304.
48. C. Müller, W. Saak, S. Doye, Eur. J. Org. Chem. 2008, 2731-2739.
49. a) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2001, 4411-4418;
50. b) F. Pohlki, I. Bytschkov, H. Siebeneicher, A. Heutling, W. A. König, S. Doye, Eur. J. Org. Chem. 2004, 1967-1972.
51. a) M. G. Clerici, F. Maspero, Synthesis 1980, 305-306;
52. b)W. A. Nugent, D. W. Ovenall, S. J. Holmes, Organometallics 1983, 2, 161-162.
53. R. Kubiak, I. Prochnow, S. Doye, Angew. Chem. 2009, 121, 1173-1176;
54. Angew. Chem. Int. Ed. 2009, 48, 1153-1156.
55. J. A. Bexrud, P. Eisenberger, D. C. Leitch, P. R. Payne, L. L. Schafer, J. Am. Chem. Soc. 2009, 131, 2116-2118.
56. U. Zucchini, E. Albizzati, U. Giannini, J. Organomet. Chem. 1971, 26, 357-372.
57. K. Gräbe, F. Pohlki, S. Doye, Eur. J. Org. Chem. 2008, 4815-4823.
58. a) B. D. Stubbert, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 6149-6167;
59. b) S. Majumder, A. L. Odom, Organometallics 2008, 27, 1174-1177.
60. a) M. C. Wood, D. C. Leitch, C. S. Yeung, J. A. Kozak, L. L. Schafer, Angew. Chem. 2007, 119, 358-362;
61. Angew. Chem. Int. Ed. 2007, 46, 354-358;
62. b) J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafer, Org. Lett. 2005, 7, 1959-1962.
63. In contrast to neutral Ti complexes, cationic Ti catalysts can be used for intramolecular hydroamination reactions of secondary aminoalkenes: a) P. D. Knight, I. Munslow, P. N. O'Shaughnessy, P. Scott, Chem. Commun. 2004, 894-895;
64. b) D. V. Gribkov, K. C. Hultzsch, Angew. Chem. 2004, 116, 5659-5663;
65. Angew. Chem. Int. Ed. 2004, 43, 5542-5546.
66. I. Prochnow, Diploma thesis, 2008, Universität Oldenburg.
67. The hydroaminoalkylation of styrene has been observed as a side reaction in base-catalyzed [LiN (SiMe3)2/TMEDA or KN (SiMe3)2/TMEDA] hydroaminations of styrene with benzhydrylamine or benzylamine: P. Horrillo-Martínez, K. C. Hultzsch, A. Gil, V. Branchadell, Eur. J. Org. Chem. 2007, 3311-3325.
68. S. Hong, S. Tian, M. V. Metz, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 14768-14783.
69. R. Severin, D. Mujahidin, J. Reimer, S. Doye, Heterocycles 2007, 74, 683-700.
70. J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158-1174.