Ruthenium-catalyzed α-(hetero)arylation of saturated cyclic amines: Reaction scope and mechanism

Chemistry - A European Journal

Volumn 19, Issue 31, 2013, Pages 10378-10387

  Peschiulli, Aldo ^a   Smout, Veerle ^a   Storr, Thomas E ^a   Mitchell, Emily A ^a   Eliáš, Zdeněk ^a   Herrebout, Wouter ^a   Berthelot, Didier ^b   Meerpoel, Lieven ^b   Maes, Bert U W ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

C H activation; homogeneous catalysis; hydrogen; nitrogen heterocycles; ruthenium

Indexed keywords

ARYLATION REACTIONS; C-H ACTIVATION; CATALYTIC AMOUNTS; EFFECT OF SUBSTITUTION; FUNCTIONALIZATIONS; HOMOGENEOUS CATALYSIS; MECHANISTIC STUDIES; NITROGEN HETEROCYCLES;

ACTIVATION ANALYSIS; AMINES; CATALYSIS; ESTERIFICATION; ESTERS; HYDROGEN; NITROGEN; REACTION KINETICS; RUTHENIUM; SUBSTRATES;

AROMATIC COMPOUNDS;

1 (PYRIDIN 2 YL)PIPERIDINE; 1-(PYRIDIN-2-YL)PIPERIDINE; AMINE; HYDROGEN; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; C H ACTIVATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HOMOGENEOUS CATALYSIS; NITROGEN HETEROCYCLES;

C H ACTIVATION; HOMOGENEOUS CATALYSIS; HYDROGEN; NITROGEN HETEROCYCLES; RUTHENIUM;

AMINES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES; PYRIDINES; RUTHENIUM;

EID: 84881391689     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204438     Document Type: Article

References (91)

1. A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932
2. G. Dyker, Angew. Chem. 1999, 111, 1808-1822
3. Angew. Chem. Int. Ed. 1999, 38, 1698-1712
4. J. A. Labinger, J. E. Bergaw, Nature 2002, 417, 507-514
5. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077-1101
6. K. Godula, D. Sames, Science 2006, 312, 67-72
7. R. G. Bergman, Nature 2007, 446, 391-393
8. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039
9. P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874-5883
10. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217
11. Angew. Chem. Int. Ed. 2009, 48, 5094-5115
12. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169
13. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092-9142
14. Angew. Chem. Int. Ed. 2012, 51, 8960-9009.
15. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025
16. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976-10011
17. Angew. Chem. Int. Ed. 2009, 48, 9792-9826
18. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624-655
19. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068-5083
20. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382-10401
21. Angew. Chem. Int. Ed. 2012, 51, 10236-10254
22. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879-5918.
23. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654-2672
24. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146
25. O. Baudoin, Chem. Soc. Rev. 2011, 40, 4902-4911.
26. L. Patel, C. Lindley, Expert Opin. Pharmacother. 2003, 4, 2279-2296
27. G. A. M. Giardina, S. Gagliardi, M. Martinelli, IDrugs 2003, 6, 758-772
28. M. Gerspacher, Prog. Med. Chem. 2005, 43, 49-103
29. P. S. Watson, B. Jiang, K. Harrison, N. Asakawa, P. K. Welch, M. Covington, N. C. Stowell, E. A. Wadman, P. Davies, K. A. Solomon, R. C. Newton, G. L. Trainor, S. M. Friedman, C. P. Decicco, S. S. Ko, Bioorg. Med. Chem. Lett. 2006, 16, 5695-5699
30. J. D. Scott, J. Weinstein, M. W. Miller, A. W. Stamford, E. J. Gilbert, Y. Xia, W. J. Greenlee, W. Li, PCT Int. Appl. WO2007084319 (A2), 2007
31. J. Ackermann, K. Bleicher, G. Ceccarelli, M. Simona, O. Chomienne, P. Mattei, T. Schulz-Gasch, PCT Int. Appl. WO2007063012 (A1), 2007
32. J. P. Michael, Nat. Prod. Rep. 2008, 25, 139-165.
33. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069-1084.
34. E. A. Mitchell, A. Peschiulli, N. Lefevre, L. Meerpoel, B. U. W. Maes, Chem. Eur. J. 2012, 18, 10092-10142.
35. P. Beak, W.-K. Lee, Tetrahedron Lett. 1989, 30, 1197-1200
36. W. F. Bailey, P. Beak, S. T. Kerrick, S. Ma, K. B. Wiberg, J. Am. Chem. Soc. 2002, 124, 1889-1896
37. T. A. Johnson, D. O. Jang, B. W. Slafer, M. D. Curtis, P. Beak, J. Am. Chem. Soc. 2002, 124, 11689-11698
38. P. O'Brien, Chem. Commun. 2008, 655-667
39. G. Barker, P. O'Brien, K. R. Campos, Org. Lett. 2010, 12, 4176-4179
40. M. J. McGrath, J. L. Bilke, P. O'Brien, Chem. Commun. 2006, 2607-2609
41. I. Coldham, D. Leonori, Org. Lett. 2008, 10, 3923-3925
42. S. Seel, T. Thaler, K. Takatsu, C. Zhang, H. Zipse, B. F. Straub, P. Mayer, P. Knochel, J. Am. Chem. Soc. 2011, 133, 4774-4777
43. I. Coldham, S. Raimbault, P. T. Chovatia, J. J. Patel, D. Leonori, N. S. Sheikh, D. T. E. Whittaker, Chem. Commun. 2008, 4174-4176
44. T. K. Beng, R. E. Gawley, J. Am. Chem. Soc. 2010, 132, 12216-12217
45. T. K. Beng, R. E. Gawley, Org. Lett. 2011, 13, 394-397.
46. Y. Shen, Z. Tan, D. Chen, X. Feng, M. Li, C.-C. Guo, C. Zhu, Tetrahedron 2009, 65, 158-163
47. G. Kumaraswamy, A. N. Murthy, A. Pitchaiah, J. Org. Chem. 2010, 75, 3916-3919
48. X.-Z. Shu, Y.-F. Yang, X.-F. Xia, K.-G. Ji, X.-Y. Liu, Y.-M. Liang, Org. Biomol. Chem. 2010, 8, 4077-4079
49. N. Shankaraiah, R. A. Pilli, L. S. Santos, Tetrahedron Lett. 2008, 49, 5098-5100
50. A. G. Condie, J. C. González-Gómez, C. R. J. Stephenson, J. Am. Chem. Soc. 2010, 132, 1464-1465.
51. Z. Li, P. D. MacLeod, C.-J. Li, Tetrahedron: Asymmetry 2006, 17, 590-597
52. G. Zhang, Y. Zhang, R. Wang, Angew. Chem. 2011, 123, 10613-10616
53. Angew. Chem. Int. Ed. 2011, 50, 10429-10432
54. H. Mitsudera, C.-J. Li, Tetrahedron Lett. 2011, 52, 1898-1900
55. D. Sureshkumar, A. Sud, M. Klussmann, Synlett 2009, 10, 1558-1561
56. O. Baslé, C.-J. Li, Org. Lett. 2008, 10, 3661-3663
57. A. Sud, D. Sureshkumar, M. Klussmann, Chem. Commun. 2009, 3169-3171
58. D. P. Hari, B. König, Org. Lett. 2011, 13, 3852-3855.
59. N. Yoshikai, A. Mieczkowski, A. Matsumoto, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2010, 132, 5568-5569
60. S. Kamijo, T. Hoshikawa, M. Inoue, Org. Lett. 2011, 13, 5928-5931
61. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 2011, 334, 1114-1117
62. T. Yoshimitsu, K. Matsuda, H. Nagaoka, K. Tsukamoto, T. Tanaka, Org. Lett. 2007, 9, 5115-5118.
63. N. Dastbaravardeh, M. Schnürch, M. D. Mihovilovic, Org. Lett. 2012, 14, 1930-1933
64. N. Dastbaravardeh, K. Kirchner, M. Schnürch, M. D. Mihovilovic, J. Org. Chem. 2013, 78, 658-672
65. S. Pan, K. Endo, T. Shibata, Org. Lett. 2011, 13, 4692-4695.
66. Y. Ishii, N. Chatani, F. Kakiuchi, S. Murai, Tetrahedron Lett. 1997, 38, 7565-7568
67. Y. Ishii, N. Chatani, F. Kakiuchi, S. Murai, Organometallics 1997, 16, 3615-3622
68. N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12882-12883
69. N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10935-10941
70. C. S. Yi, S. Y. Yun, Organometallics 2004, 23, 5392-5395.
71. S. J. Pastine, D. V. Gribkov, D. Sames, J. Am. Chem. Soc. 2006, 128, 14220-14221.
72. For a detailed review on the use of directing groups in catalysis, see:, G. Rousseau, B. Breit, Angew. Chem. 2011, 123, 2498-2543
73. Angew. Chem. Int. Ed. 2011, 50, 2450-2494.
74. S. D. Bergman, T. E. Storr, H. Prokopcova, K. Aelvoet, G. Diels, L. Meerpoel, B. U. W. Maes, Chem. Eur. J. 2012, 18, 10393-10398.
75. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2903.
76. F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936-5945.
77. H. Prokopcová, S. D. Bergman, K. Aelvoet, V. Smout, W. Herrebout, B. Van der Veken, L. Meerpoel, B. U. W. Maes, Chem. Eur. J. 2010, 16, 13063-13067.
78. L. Ackermann, Top. Organomet. Chem. 2007, 24, 35-60.
79. J. A. Joule, K. Mills, Heterocyclic Chemistry, 4 th ed., Blackwell Science, Oxford, 2000
80. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles, 2 nd ed., Wiley-VCH, Weinheim, 2003
81. L. D. Quin, J. Tyrell, Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals, Wiley, Hoboken, NJ, 2010.
82. For a review about C-H activation/C-B bond formation through oxidative addition of a dialkoxyborane species to transition metals, see:, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2003, 680, 3-11.
83. 2 gas formation during transition-metal-catalyzed C-H functionalization processes was previously described for C-B bond forming reactions; see:, I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890-931.
84. R. H. Crabtree, Acc. Chem. Res. 1990, 23, 95-101
85. D. M. Heinekey, W. J. Oldham, Jr., Chem. Rev. 1993, 93, 913-926.
86. S. Hawkeswood, D. W. Stephan, Dalton Trans. 2005, 680, 2182-2187
87. V. Montiel-Palma, M. Lumbierres, B. Donnadieu, S. Sabo-Etienne, B. Chaudret, J. Am. Chem. Soc. 2002, 124, 5624-5625
88. M. Arrowsmith, M. S. Hill, T. Hadlington, G. Kociok-Köhn, C. Weetman, Organometallics 2011, 30, 5556-5559.
89. Ruthenium in Organic Synthesis (Ed.:, S.-I. Murahashi,), Wiley-VCH, Weinheim, 2004.
90. For a detailed discussion dealing with KIE in transition-metal-catalyzed C-H bond functionalization, see:, E. M. Simmons, J. F. Hartwig, Angew. Chem. 2009, 124, 3120-3126
91. Angew. Chem. Int. Ed. 2012, 51, 3066-3072.