2-pyridyl tosylate derivatives-Building blocks for structural diversity via transition metal catalysis

Israel Journal of Chemistry

Volumn 50, Issue 5-6, 2010, Pages 558-567

  Lindhardt, Anders T ^a   Gøgsig, Thomas M ^a   Gauthier, Delphine ^a   Lupp, Daniel ^a   Mantel, Mette Louise Hallager ^a   Bjerglund, Klaus M ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

2 pyridyl tosylate derivatives; cross coupling; heterocycles; Mizoroki Heck reaction; transition metal catalysis

Indexed keywords

EID: 78650638746     PISSN: 00212148     EISSN: 18695868     Source Type: Journal    
DOI: 10.1002/ijch.201000031     Document Type: Article

References (127)

1. V. F. Slagt, A. H. M. de Vries, J. G. de Vries, R. M. Kellogg, Org. Process Res. Dev. 2010, 14, 30-47
2. H. J. Roth, A. Kleemann, in Pharmaceutical Chemistry, Volume 1: Drug Synthesis, John Wiley and Sons, NY, 1988
3. F. Sha, X. Huang, Angew. Chem. 2009, 121, 3510-3513
4. Angew. Chem. Int. Ed. 2009, 48, 3458-3461
5. M. Movassaghi, M. D. Hill, O. K. Ahmad, J. Am. Chem. Soc. 2007, 129, 10096-10097
6. A. S. Karpov, E. Merkul, F. Rominger, T. J. J. Müller., Angew. Chem., Int. Ed. 2005, 44, 6951-6956.
7. M. C. Bagley, C. Glover, E. A. Merritt, Synlett 2007, 2459-2482
8. M. D. Hill, M. Movassaghi, Chem. Eur. J. 2008, 14, 6836-6844
9. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles-Structure, Reactions, Synthesis and Application (translated by H. Suschitzky, J. Suschitzky), Wiley-VCH, Weinheim, 2003.
10. O. Hromatka, D. Binder, R. Pfister, P. Zeller, (Hoffmann-La Roche Inc.), US4076709 (A), 1978
11. K. Hino, H. Nakamura, Y. Nagai, H. Uno, H. Nishimura., J. Med. Chem. 1983, 26, 222-226
12. A. S. Kalgutkar, H. L. Hatch, F. Kosea, H. T. Nguyen, E. F. Choo, K. F. McClure, T. J. Taylor, K. R. Henne, A. V. Kuperman, M. A. Dombroski, M. A. Letavic., Biopharm. Drug Dispos. 2006, 27, 371-386
13. U. Mueller, (Syngenta Participations AG), WO2005/21490 (A2), 2005
14. R. Imhof, E. Kyburz, (Hoffmann-La Roche Inc.), US4764522 A1, 1988
15. B. Orzeszko, Z. Kazimierczuk, J. K. Maurin, A. E. Laudy, B. J. Starosciak, J. Vilpo, L. Vilpo, J. Balzarini, A. Orzeszko, Farmaco 2004, 59, 929-938.
16. For selected references see
17. R. Kozlowski, M. Wladyka-Przybylak, Polym. Adv. Technol. 2008, 19, 446-453
18. T. Yamamoto, S. Watanabe, H. Fukumoto, M. Sato, T. Tanaka, Macromol. Rapid Commun. 2006, 27, 317-321
19. S. E. Mallakpour, A.-R. Hajipour, A.-R. Mahdavian, S. Rhoee, J. Appl. Polym. Sci. 2000, 10, 2507-2513
20. F. Lu, Polym. Rev. 1998, 38, 143-205
21. J. W. Mintmire, C. T. White, M. L. Elert, Synthetic Metals, 1986, 16, 235-243.
22. For selected examples see
23. M. B. Nielsen, S. L. Broman, M. Å. Petersen, A. S. Andersson, T. S. Jensen, K. Kilsã, A. Kadziola, Pure Appl. Chem. 2010, 82, 843-852
24. J. Areephong, J. H. Hurenkamp, M. T. W. Milder, A. Meetsma, J. L. Herek, W. R. Browne, B. L. Feringa, Org. Lett. 2009, 11, 721-724
25. H. Tian, S. Yang., Chem. Soc. Rev. 2004, 33, 85-97
26. B. L. Feringa, Ed., Molecular Switches, Wiley-VCH, Weinheim, 2001.
27. For books on the construction of heterocycles using Pd-catalysis see
28. Palladium in Heterocyclic Chemistry, Vol. 26 (Eds.:, J. J. Li, G. W. Gribble,), Pergamon, Amsterdam, 2006
29. Kotschy, G. Timári, Heterocycles from Transition Metal Catalysis, Vol. 28 (Eds.:, B. James, P. W. N. M. van Leeuwen,), Springer, Dordrecht, 2005.
30. For recent examples see
31. M. Zhang, Adv. Synth. Catal. 2009, 351, 2243-2270
32. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198
33. G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644-4680
34. L. Melzig, A. Metzger, P. Knochel., J. Org. Chem. 2010, 75, 2131-2133
35. S. Wacharasindhu, S. Bardhan, Z.-K. Wan, K. Tabei, T. S. Mansour., J. Am. Chem. Soc. 2009, 131, 4174-4175, and references therein.
36. S. L Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23-39
37. A. O. King, N. Yasuda., Top. Organomet. Chem. 2004, 6, 205-245.
38. K. Billingsly, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366
39. A. Markham, K. L. Goa, Drugs 1997, 54, 299-311
40. R. Capdeville, E. Buchdunger, J. Zimmermann, A. Matter, Nat. Rev. Drug Discovery 2002, 1, 493-502
41. J. Boren, M. Cascante, S. Marin, B. Comin-Anduix, J. J. Centelles, S. Lim, S. Bassilian, S. Ahmed, W. N. Lee, L. G. Boros, J. Biol. Chem. 2001, 276, 37747-37753.
42. For examples see
43. R. Martin, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3844-3845
44. V. P. Mehta, S. G. Modha, E. Van der Eycken, J. Org. Chem. 2009, 74, 6870-6873
45. Z. Xi, B. Liu, W. Chen, J. Org. Chem. 2008, 73, 3954-3957
46. G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2009, 48, 205-209
47. M. G. Organ, M. Abdel-Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O'Brian, C. Valente, Chem. Eur. J. 2007, 13, 150-157.
48. For examples see
49. W.-J. Zhou, K.-H. Wang, J.-X. W, J. Org. Chem. 2009, 74, 5599-5602
50. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
51. B. S. Yong, S. P. Nolan, Chemtracts: Org. Chem. 2003, 16, 205-227
52. N. T. S. Phan, M. Van Der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679
53. M. Heller, U. S. Schubert, J. Org. Chem. 2002, 67, 8269-8272.
54. For examples see
55. B. H. Kaae, P. Krogsgaard-Larsen, T. N. Johansen, J. Org. Chem. 2004, 69, 1401-1404
56. S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380-7382
57. G. Manolikakes, M. A. Schade, C. M. Hernandez, H. Mayr, P. Knochel, Org. Lett. 2008, 10, 2765-2768.
58. For examples see
59. A. S. Guram, A. O. King, J. G. Allen, X. Wang, L. B. Schenkel, J. Chan, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, P. J. Reider, Org. Lett. 2006, 8, 1787-1789
60. G. A. Molander, A. R. Brown, J. Org. Chem. 2006, 71, 9681-9686
61. A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen, M. J. Martinelli, J. Org. Chem. 2007, 72, 5104-5112
62. N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. 2006, 118, 1304-1306
63. Angew. Chem. Int. Ed. 2006, 45, 1282-1284.
64. For examples see
65. Q. Shen, T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 6586-6596
66. T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848-13849
67. Q. Shen, J. F. Hartwig, Org. Lett. 2008, 10, 4109-4112
68. M. D. Charles, P. Schultz, S. L. Buchwald, Org. Lett. 2005, 7, 3965-3968
69. K. Dooleweerdt, B. P. Fors, S. L. Buchwald., Org. Lett. 2010, 12, 2350-2353
70. G.-Y. Gao, Y. Chen, X. P. Zhang., Org. Lett. 2004, 6, 1837-1840
71. G. B. W. L. Ligthart, H. Ohkawa, R. P. Sijbesma, E. W. Meijer., J. Org. Chem. 2006, 71, 375-378.
72. M. Tobisu, N. Chatani, Angew. Chem. 2009, 121, 3617-3620
73. Angew. Chem. Int. Ed. 2009, 48, 3565-3568.
74. C. Shi, C. C. Aldrich, Org. Lett. 2010, 12, 2286-2289.
75. T. M. Gøgsig, L. S. Søbjerg, A. T. Lindhardt, K. L. Jensen, T. Skrydstrup, J. Org. Chem. 2008, 73, 3404-3410.
76. J. R. Naber, B. P. Fors, X. Wu, J. T. Gunn, S. L. Buchwald, Heterocycles 2010, 80, 1215-1226
77. R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754-2755
78. L. Zhang, J. Wu, J. Am. Chem. Soc. 2008, 130, 12250-12251
79. C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem. 2008, 73, 7731-7734
80. L. Zhang, T. Meng, J. Wu, J. Org. Chem. 2007, 72, 9346-9349
81. L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457-3460
82. M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364-9370
83. A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704-8705.
84. A. L. Hansen, T. Skrydstrup., J. Org. Chem. 2005, 70, 5997-6003.
85. The intermediacy of such a cationic palladium complex is mandatory in order to obtain high degrees of regioselectivity, see
86. J. Mo, L. Xu, J. Xiao, J. Am. Chem. Soc. 2005, 127, 751-760
87. F. Ozawa, A. Kubo, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417-1419
88. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7
89. M. Ludwig, S. Stromberg, M. Svensson, B. Akermark, Organometallics 1999, 18, 970-975
90. M. Larhed, A. Hallberg, in Handbook of Organopalladium Chemistry for Organic Synthesis; (Ed.:, E. Negishi,), John Wiley & Sons, NY, 2002.
91. A. L. Hansen, T. Skrydstrup, Org. Lett. 2005, 7, 5585-5587.
92. A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skrydstrup, Angew. Chem. 2006, 118, 3427-3431
93. Angew. Chem. Int. Ed. 2006, 45, 3349-3353
94. J.-P. Ebran, A. L. Hansen, T. M. Gøgsig, T. Skrydstrup, J. Am. Chem. Soc. 2007, 129, 6931-6942.
95. LiCl is thought to direct the reaction through a neutral mechanism which is preferred when coupling to electron-poor olefins. See ref. [22] and, A. L. Hansen, J.-P. Ebran, T. M. Gøgsig, T. Skrydstrup, J. Org. Chem. 2007, 72, 6464-6472.
96. For recent examples of 2-pyridyl chlorides in Pd-catalysis see
97. I. Malik, M. Hussain, A. Ali, S.-M. T. Toguem, F. Z. Basha, C. Fisher, P. Langer, Tetrahedron 2010, 66, 1637-1642
98. W. A. Herrebout, N. Nagels, S. Verbeeck, B. J. van der Veken, B. U. W. Maes, Eur. J. Org. Chem. 2010, 3152-3158 and references sited therein.
99. For selected references on the tautomeric equilibrium of hydroxypyridines, see
100. H. B. Schlegel, P. Gund, E. M. Fluder, J. Am. Chem. Soc. 1982, 104, 5347-5351
101. R. H. Cox, A. A. Bothner-By, J. Phys. Chem. 1969, 73, 2465-2468.
102. T. M. Gøgsig, A. T. Lindhardt, M. Dekhane, J. Grouleff, T. Skrydstrup, Chem. Eur. J. 2009, 15, 5950-5955.
103. For selected examples, see
104. T. M. Gøgsig, A. T. Lindhardt, T. Skrydstrup, Org. Lett. 2009, 11, 4886-4888
105. J. J. Manclús, J. Primo, A. Montoya, J. Agric. Food Chem. 1996, 44, 4052-4062.
106. M. L. H. Mantel, A. T. Lindhardt, D. Lupp, T. Skrydstrup, Chem. Eur. J. 2010, 16, 5437-5442.
107. S. Kramer, K. Dooleweerdt, A. T. Lindhardt, M. Rottländer, T. Skrydstrup, Org. Lett. 2009, 11, 4208-4211.
108. H. Siegel, R. B. Martin., Chem. Rev. 1982, 82, 385-426.
109. R. H. Crabtree, in The organometallic chemistry of the transition metals, John Wiley & Sons, NY, 2009
110. For an excellent review on palladium catalyzed carbonylation reactions using CO see:, A. Brennenführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, 4114-4133, and references therein.
111. J. R. Martinelli, T. P. Clark, D. A. Watson, R. H. Munday, S. L. Buchwald, Angew. Chem. 2007, 119, 8612-8615
112. Angew. Chem. Int. Ed. 2007, 46, 8460-8463.
113. W. Mägerlein, A. F. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940-2943
114. Angew. Chem. Int. Ed. 2001, 40, 2856-2859.
115. A. Reichelt, J. R. Falsey, R. M. Rzasa, O. R. Thiel, M. M. Achmatowicz, R. D. Larsen, D. Zhang, Org. Lett. 2010, 12, 792.
116. G. Jones, Adv. Heterocycl. Chem. 2002, 83, 1.
117. For selected references on iron catalysis see
118. A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635
119. Angew. Chem. Int. Ed. 2002, 41, 609-612
120. A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863
121. T. Hatakeyama, M. Nakamura, J. Am. Chem. Soc. 2007, 129, 9844-9845
122. J. Quintin, X. Franck, R. Hocquemiller, B. Figadère, Tetrahedron Lett. 2002, 43, 3547-3549
123. G. Cahiez, H. Avedissian, Synthesis 1998, 1199-1205.
124. For related work on heteroaromatic phosphate electrophiles see
125. M. Chaignaud, I. Gillaizeau, N. Ouhamou, G. Coudert, Tetrahedron 2008, 64, 8059-8066
126. E. Claveau, I. Gillaizeau, J. Blu, A. Bruel, G. Coudert, J. Org. Chem. 2007, 72, 4832-4836
127. D. Mousset, I. Gillaizeau, A. Sabatié, P. Bouyssou, G. Coudert, J. Org. Chem. 2006, 71, 5993-5999.