Direct synthesis of pyrroles by dehydrogenative coupling of β-aminoalcohols with secondary alcohols catalyzed by ruthenium pincer complexes

Angewandte Chemie - International Edition

Volumn 52, Issue 14, 2013, Pages 4012-4015

  Srimani, Dipankar ^a   Ben David, Yehoshoa ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

dehydrogenation; homogeneous catalysis; pincer complex; pyrroles; ruthenium

Indexed keywords

C-C BOND FORMATION; DEHYDROGENATIVE COUPLING; DIRECT SYNTHESIS; ENVIRONMENTALLY-FRIENDLY; HOMOGENEOUS CATALYSIS; PINCER COMPLEXES; PYRROLES; SECONDARY ALCOHOLS;

CATALYSIS; DEHYDROGENATION; REACTION KINETICS; RUTHENIUM; SYNTHESIS (CHEMICAL);

RUTHENIUM COMPOUNDS;

AMINOALCOHOL; CARBON; COORDINATION COMPOUND; NITROGEN; PYRROLE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINO ALCOHOLS; CARBON; CATALYSIS; COORDINATION COMPLEXES; NITROGEN; PYRROLES; RUTHENIUM;

EID: 84875696858     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300574     Document Type: Article

References (98)

1. V. Estévez, M. Villacampa, J. C. Menéndez, Chem. Soc. Rev. 2010, 39, 4402
2. F. R. de Sa Alves, E. J. Barreiro, C. A. M. Fraga, Mini-Rev. Med. Chem. 2009, 9, 782
3. H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264
4. A. Hall, S. Atkinson, S. H. Brown, I. P. Chessell, A. Chowdhury, G. M. P. Giblin, P. Goldsmith, M. P. Healy, K. S. Jandu, M. R. Johnson, A. D. Michel, A. Naylor, J. A. Sweeting, Bioorg. Med. Chem. Lett. 2007, 17, 1200
5. F. Bellina, R. Rossi, Tetrahedron 2006, 62, 7213
6. F. Micheli, R. Di Fabio, R. Benedetti, A. M. Capelli, P. Cavallini, P. Cavanni, S. Davalli, D. Donati, A. Feriani, S. Gehanne, M. Hamdan, M. Maffeis, F. M. Sabbatini, M. E. Tranquillini, M. V. A. Viziano, Farmaco 2004, 59, 175.
7. N. Amishiro, S. Nagamura, E. Kobayashi, A. Okamoto, K. Gomi, H. Saito, Chem. Pharm. Bull. 1999, 47, 1393
8. N. Amishiro, S. Nagamura, E. Kobayashi, A. Okamoto, K. Gomi, M. Okabe, H. Saito, Bioorg. Med. Chem. 2000, 8, 1637
9. V. J. Demopoulos, E. Rekka, J. Pharm. Sci. 1995, 84, 79
10. R. W. Bürli, D. McMinn, J. A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka, H. E. Moser, Bioorg. Med. Chem. Lett. 2004, 14, 1253
11. D. Wang, X. Hu, G. Zhao, Int. J. Food Sci. Technol. 2008, 43, 1880
12. M. Del Poeta, W. A. Schell, C. C. Dykstra, S. Jones, R. R. Tidwell, A. Czarny, M. Bajic, A. Kumar, D. Boykin, J. R. Perfect, Antimicrob. Agents Chemother. 1998, 42, 2495
13. M. Wang, H. Xu, T. Liu, Q. Feng, S. Yu, S. Wang, Z. Li, Eur. J. Med. Chem. 2011, 46, 1463.
14. P. Pfluger, M. Krounbi, G. B. Street, G. Weiser, J. Chem. Phys. 1983, 78, 3212
15. I. F. Gimenez, O. L. Alves, J. Braz. Chem. Soc. 1999, 10, 167
16. J. R. Reynolds, P. A. Poropatic, R. L. Toyooka, Macromolecules 1987, 20, 958
17. R. E. Nizurski-Mann, M. P. Cava, Heterocycles 1992, 34, 2003
18. S. S. P. Chou, Y.-H. Yeh, Tetrahedron Lett. 2001, 42, 1309
19. C. D'Silva, D. A. Walker, J. Org. Chem. 1998, 63, 6715
20. B. P. J. de Lacy Costello, P. Evans, N. Guernion, N. M. Ratcliffe, P. S. Sivanand, G. C. Teare, Synth. Met. 2000, 114, 181.
21. A. W. Trautwein, R. D. Sümuth, G. Jung, Bioorg. Med. Chem. Lett. 1998, 8, 2381
22. L. Calvo, A. González-Ortega, M. C. Sañudo, Synthesis 2002, 2450
23. V. S. Matiychuk, R. L. Martyak, N. D. Obushak, Y. V. Ostapiuk, N. I. Pidlypnyi, Chem. Heterocycl. Compd. 2004, 40, 1218.
24. A. Alberola, A. G. M. L. Ortega, C. Sadaba, C. Sanudo, Tetrahedron 1999, 55, 6555
25. I. Elghamry, Synth. Commun. 2002, 32, 897
26. J. M. Manley, M. J. Kalman, B. G. Conway, C. C. Ball, J. L. Havens, R. J. Vaidyanathan, J. Org. Chem. 2003, 68, 6447
27. R. K. Bellingham, J. S. Carey, N. Hussain, D. O. Morgan, P. Oxley, L. C. Powling, Org. Process Res. Dev. 2004, 8, 279
28. C. M. Shiner, T. D. Lash, Tetrahedron 2005, 61, 11628.
29. R. A. Jones, G. P. Been, The Chemistry of Pyrroles, Academic Press, New York, 1977, chap. 3
30. P. K. Chiu, K. H. Lui, P. N. Maini, M. P. Sammes, J. Chem. Soc. Chem. Commun. 1987, 109
31. P. K. Chiu, M. P. Sannes, Tetrahedron 1990, 46, 3439
32. B. K. Banik, S. Samajdar, I. Banik, J. Org. Chem. 2004, 69, 213
33. J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, W. Su, Tetrahedron Lett. 2006, 47, 5383
34. G. Minetto, L. F. Raveglia, A. Sega, M. Taddei, Eur. J. Org. Chem. 2005, 5277.
35. H. Shiraishi, T. Nishitani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 1998, 63, 6234
36. Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S. Uemura, Angew. Chem. 2003, 115, 2785
37. Angew. Chem. Int. Ed. 2003, 42, 2681
38. R. Dhawan, B. A. Arndtsen, J. Am. Chem. Soc. 2004, 126, 468
39. D. Tejedor, D. González-Cruz, F. García-Tellado, J. J. Marrero-Tellado, M. L. Rodríguez, J. Am. Chem. Soc. 2004, 126, 8390
40. Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804
41. O. V. Larionov, A. Meijere, Angew. Chem. 2005, 117, 5809
42. Angew. Chem. Int. Ed. 2005, 44, 5664
43. D. J. St. Cyr, N. Martin, B. A. Arndtsen, Org. Lett. 2007, 9, 449
44. M. Shimizu, A. Takahashi, S. Kawai, Org. Lett. 2006, 8, 3585
45. I. Bergner, T. Opatz, J. Org. Chem. 2007, 72, 7083
46. C. V. Galliford, K. A. Scheidt, J. Org. Chem. 2007, 72, 1811
47. B. Khalili, P. Jajarmi, B. M. M. Eftekhari-SisHashemi, J. Org. Chem. 2008, 73, 2090
48. X. Chen, L. Hou, X. Li, Synlett 2009, 828
49. E. Merkul, C. Boersch, W. Frank, T. J. J. Müller, Org. Lett. 2009, 11, 2269
50. Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 351, 129.
51. C. A. Merlic, A. Baur, C. C. Aldrich, J. Am. Chem. Soc. 2000, 122, 7398
52. A. V. Kel'in, A. W. Sromek, V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 2074
53. R. U. Braun, K. Zeitler, T. J. J. Muller, Org. Lett. 2001, 3, 3297
54. H. Takaya, S. Kojima, S.-l. Murahashi, Org. Lett. 2001, 3, 421
55. Y. Wang, S. Zhu, Org. Lett. 2003, 5, 745
56. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127
57. B. Ramanathan, A. J. Keith, D. Armstrong, A. L. Odom, Org. Lett. 2004, 6, 2957
58. A. I. Siriwardana, K. K. A. D. S. Kathriarachchi, I. Nakamura, I. D. Gridnev, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 13898
59. S. Kamijo, C. Kanazawa, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 9260
60. D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260
61. R. P. Wurz, A. B. Charette, Org. Lett. 2005, 7, 2313
62. R. Martín, M. R. Rivero, S. L. Buchwald, Angew. Chem. 2006, 118, 7237
63. Angew. Chem. Int. Ed. 2006, 45, 7079
64. J. F. Hartwig, Synlett 2006, 1283
65. L. Lu, G. Chen, S. Ma, Org. Lett. 2006, 8, 835
66. J. T. Binder, S. F. Kirsch, Org. Lett. 2006, 8, 2151
67. K. Hiroya, S. Matsumoto, M. Ashikawa, K. Ogiwara, T. Sakamoto, Org. Lett. 2006, 8, 5349
68. D. J. S. Cyr, B. A. Arndtsen, J. Am. Chem. Soc. 2007, 129, 12366
69. F. M. Istrate, F. Gagosz, Org. Lett. 2007, 9, 3181
70. X.-Z. Shu, X.-Y. Liu, H.-Q. Xiao, K.-G. Ji, L.-N. Guo, Y.-M. Liang, Adv. Synth. Catal. 2008, 350, 243
71. A. Aponick, C.-Y. Li, J. Malinge, E. F. Marques, Org. Lett. 2009, 11, 4624
72. S. Maiti, S. Biswas, U. Jana, J. Org. Chem. 2010, 75, 1674
73. W. Liu, H. Jiang, L. Huang, Org. Lett. 2010, 12, 312
74. M. Zhang, H. Neumann, M. Beller, Angew. Chem. 2013, 125, 625
75. Angew. Chem. Int. Ed. 2013, 52, 597
76. N. D. Schley, G. E. Dobereiner, R. H. Crabtree, Organometallics 2011, 30, 4174.
77. J. Zhang, M. Gandelman, L. J. W. Shimon, D. Milstein, Organometallics 2004, 23, 4026
78. J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, J. Am. Chem. Soc. 2005, 127, 10840
79. J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem. 2006, 118, 1131
80. Angew. Chem. Int. Ed. 2006, 45, 1113
81. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790
82. D. Milstein, Top. Catal. 2010, 53, 915
83. B. Gnanaprakasam, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2010, 352, 3169
84. B. Gnanaprakasam, D. Milstein, J. Am. Chem. Soc. 2011, 133, 1682
85. C. Gunanathan, D. Milstein, Acc. Chem. Res. 2011, 44, 588
86. D. Srimani, M. Feller, Y. Ben-David, D. Milstein, Chem. Commun. 2012, 48, 11853.
87. C. Gunanathan, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2009, 131, 3146
88. C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789
89. Angew. Chem. Int. Ed. 2008, 47, 8661
90. C. Gunanathan, B. Gnanaprakasam, M. A. Iron, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2010, 132, 14763.
91. B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. 2010, 122, 1510
92. Angew. Chem. Int. Ed. 2010, 49, 1468.
93. D. Srimani, E. Balaraman, B. Ganaprakasam, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2012, 354, 2403.
94. B. Gnanaprakasam, E. Balaraman, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 12448
95. Angew. Chem. Int. Ed. 2011, 50, 12240.
96. S. Michlik, R. Kempe, Nat. Chem. 2013, 5, 140.
97. E. Balaraman, B. Ganaprakasam, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2010, 132, 16756
98. E. Balaraman, C. Gunanathan, J. Zhang, L. J. W. Shimon, D. Milstein, Nat. Chem. 2011, 3, 609.