Palladium-catalyzed direct arylation of heteroarenes with aryl mesylates

Chemistry - A European Journal

Volumn 17, Issue 3, 2011, Pages 761-765

  So, Chau Ming ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

aryl mesylates; C H activation; direct arylation; heterocycles; palladium

Indexed keywords

ARYLATIONS; C-H ACTIVATION; DIRECT ARYLATION; ELECTROPHILES; FUNCTIONALIZATIONS; HETEROARENES; HETEROCYCLES; MESYLATES; REACTION CONDITIONS;

ACTIVATION ANALYSIS; CHEMICAL REACTIONS; PALLADIUM;

AROMATIC COMPOUNDS;

HETEROCYCLIC COMPOUND; MESYLIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CATALYSIS; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MESYLATES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 78651446257     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002354     Document Type: Article

References (122)

1. Metal-Catalyzed Cross-Coupling Reactions, Vols.1-2, 2 nd ed., (Eds.: A. deMeijere, F. Diederich,), Wiley-VCH, Weinheim 2004
2. M. Beller, C. Bolm, Transition Metals for Organic Synthesis Building Blocks and Fine Chemicals, Vols. 1-2, 2 nd ed., Wiley-VCH, Weinheim, 2004
3. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359
4. J. Tsuji, Palladium Reagents and Catalysts, 2 nd ed., Wiley, New York, 2004
5. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133
6. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651
7. A. Roglans, A. Pla-Quintana, M. Moreno-Manas, Chem. Rev. 2006, 106, 4622
8. Modern Arylation Methods (Ed.:, L. Ackermann,), Wiley-VCH, Weinheim, 2009.
9. For reviews concerning the applications of cross-coupling in preparing pharmaceutically useful intermediates, see K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516
10. Angew. Chem. Int. Ed. 2005, 44, 4442
11. K. C. Nicolaou, E. J. Sorensen, Classic in Total Synthesis II, More Targets, Strategies and Methods, Wiley-VCH, Weinheim, 2003.
12. For recent reviews, see B. J. Li, S. D. Yang, Z. J. Shi, Synlett 2008, 949-957
13. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
14. T. Satoh, M. Miura, Top. Organomet. Chem. 2007, 24, 61
15. L. Ackermann, Top. Organomet. Chem. 2007, 24, 35
16. D. Kalyani, M. S. Sanford, Top. Organomet. Chem. 2007, 24, 85
17. S. Pascual, P. deMendoza, A. M. Echavarren, Org. Biomol. Chem. 2007, 5, 2727
18. L. Ackermann, Synlett 2007, 0507
19. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
20. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
21. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
22. Angew. Chem. Int. Ed. 2009, 48, 5094
23. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
24. Angew. Chem. Int. Ed. 2009, 48, 9792
25. F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269
26. L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673
27. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
28. G. Dyker, Handbook of Ci-H Transformations, Wiley-VCH, Weinheim, 2005.
29. For recent superb advancements in Ci-H functionalization, see D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
30. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
31. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315.
32. For selected recent references on the Pd-catalyzed direct functionalization of heteroarenes by using ArI and ArBr, see T. Okazawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 5286
33. B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050
34. G. L. Turner, J. A. Morris, M. F. Greaney, Angew. Chem. 2007, 119, 8142
35. Angew. Chem. Int. Ed. 2007, 46, 7996
36. X. Wang, D. V. Gribkov, D. Sames, J. Org. Chem. 2007, 72, 1476
37. N. Lebrasseur, I. Larrosa, J. Am. Chem. Soc. 2008, 130, 2926
38. L.-C. Campeau, M. Bertrand-Laperle, J.-P. Leclerc, E. Villemure, S. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 3276
39. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848
40. S. Yanagisawa, K. Ueda, H. Sekizawa, K. Itami, J. Am. Chem. Soc. 2009, 131, 14622
41. J.-P. Leclerc, K. Fagnou, Angew. Chem. 2006, 118, 7945
42. Angew. Chem. Int. Ed. 2006, 45, 7781
43. N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972
44. A. Battace, M. Lemhadri, T. Zair, H. Doucet, M. Santelli, Organometallics 2007, 26, 472
45. A. L. Gottumukkala, H. Doucet, Eur. J. Inorg. Chem. 2007, 3629
46. D. G. Hulcoop, M. Lautens, Org. Lett. 2007, 9, 1761
47. L. Ackermann, S. Barfüer, Synlett 2009, 808
48. F. Shibahara, E. Yamaguchi, T. Murai, Chem. Commun. 2010, 46, 2471; for the Pd-catalyzed direct functionalization of arenes by using ArI and ArBr, see
49. M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496
50. D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330; for selected recent Ni catalyses, see
51. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733
52. H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737.
53. For activated ArCl, see:, Y. Aoyagi, A. Inoue, I. Koizumi, R. Hashimoto, K. Tokunaga, K. Gohma, J. Komatsu, K. Sekine, A. Miyafuji, J. Kunoh, R. Honma, Y. Akita, A. Ohta, Heterocycles 1992, 33, 257.
54. S. Pivasa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1988, 61, 467
55. I. Čeraňa, R. Pohl, B. Klepetářová, M. Hocek, Org. Lett. 2006, 8, 5389
56. F. Bellina, S. Cauteruccio, R. Rossi, Eur. J. Org. Chem. 2006, 1379; for Zn-salts-assisted pathways, see
57. R. D. Rieth, N. P. Mankad, E. Calimano, J. P. Sadighi, Org. Lett. 2004, 6, 3981.
58. A. Chiong, O. Daugulis, Org. Lett. 2007, 9, 1449.
59. For a review, see:, Z. Gilson, R. Larock, Chem. Rev. 2006, 106, 4644.
60. For examples of Pd-catalyzed direct arylations of aromatic derivatives through Ci-H activation by using aryl triflates, see T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki, J. Am. Chem. Soc. 1994, 116, 1004
61. G. Brigmann, A. Wuzik, J. Kraus, K. Peters, E.-M. Peters, Tetrahedron Lett. 1998, 39, 1545
62. L. Wang, P. B. Shevlin, Tetrahedron Lett. 2000, 41, 285
63. Y. Kametani, T. Satoh, M. Miura, M. Nomura, Tetrahedron Lett. 2000, 41, 2655
64. H. Nishioka, Y. Shoujiguchi, H. Abe, Y. Takeuchi, T. Harayama, Heterocycles 2004, 64, 463
65. O. Hara, T. Nakamura, F. Sato, K. Makino, Y. Hamada, Heterocycles 2006, 68, 1
66. M. Brenner, G. Mayer, A. Terpin, W. Steglich, Chem. Eur. J. 1997, 3, 70.
67. For a mechanistic study on the oxidative addition of ArOTs by using Pd complexes, see:, A. H. Roy, J. F. Hartwig, Organometallics 2004, 23, 194.
68. Nickel-catalyzed cross coupling of aryl sulfonates were reported in a pioneering study, see V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 1060
69. V. Percec, G. M. Golding, J. Smidrkal, O. Weichold, J. Org. Chem. 2004, 69, 3447
70. D. Zim, V. R. Lando, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049
71. Z. Y. Tang, Q. S. Hu, J. Am. Chem. Soc. 2004, 126, 3058.
72. For Suzuki couplings with ArOTs substrates, see H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818
73. L. Zhang, T. Meng, J. Wu, J. Org. Chem. 2007, 72, 9346
74. C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem. 2008, 73, 7731; for Kumada coupling, see
75. A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704
76. M. E. Limmert, A. H. Roy, J. F. Hartwig, J. Org. Chem. 2005, 70, 9364
77. L. Ackermann, A. Althammer, Org. Lett. 2006, 8, 3457; for Ci-N bond coupling, see
78. X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653
79. T. Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 13848; for Sonogashira couplings by using activated ArOTs, see
80. D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175
81. Angew. Chem. Int. Ed. 2003, 42, 5993
82. O. R'kyek, N. Halland, A. Lindenschmidt, J. Alonso, P. Lindemann, M. Urmann, M. Nazaré, Chem. Eur. J. 2010, 16, 9986; for Hiyama couplings, see
83. L. Zhang, J. Wu, J. Am. Chem. Soc. 2008, 130, 12250; for carbonylation, see
84. R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754.
85. For ArOMs in Ci-N bond formation, see C. M. So, Z. Zhou, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 6502
86. Angew. Chem. Int. Ed. 2008, 47, 6402
87. B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 13552; for ArOMs in Suzuki coupling, see
88. C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 8179
89. Angew. Chem. Int. Ed. 2008, 47, 8059
90. B. Bhayana, B. P. Fors, S. L. Buchwald, Org. Lett. 2009, 11, 3954
91. W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, J. Org. Chem. 2010, 75, 5109; for Hiyama coupling, see
92. L. Zhang, J. Qing, P. Yang, J. Wu, Org. Lett. 2008, 10, 4971
93. C. M. So, H. W. Lee, C. P. Lau, F. Y. Kwong, Org. Lett. 2009, 11, 317; for Sonogashira coupling, see
94. P. Y. Choy, W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, Chem. Eur. J. 2010, 16, 9982; for cyanation, see
95. P. Y. Yeung, C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. 2010, 122, 9102
96. Angew. Chem. Int. Ed. 2010, 49, 8918.
97. For Buchwald's initial development of X-Phos in Ci-C coupling reactions, see reference[13a].
98. L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 207
99. Angew. Chem. Int. Ed. 2009, 48, 201.
100. a=-14.9), see: Ionization Constants of Organic Acids in Solution, IUPAC Chemical Data Series No. 23 (Eds.:, E.P. Serjeant, B. Dempsey,), Pergamon Press, Oxford, 1979.
101. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315
102. Angew. Chem. Int. Ed. 2000, 39, 4153.
103. A. Zapf, M. Beller, Chem. Commun. 2005, 431.
104. C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2007, 9, 2795; for other related types of indolyl phosphines, see
105. H. W. Lee, F. L. Lam, C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, Angew. Chem. 2009, 121, 7572
106. Angew. Chem. Int. Ed. 2009, 48, 7436
107. C. M. So, W. K. Chow, P. Y. Choy, C. P. Lau, F. Y. Kwong, Chem. Eur. J. 2010, 16, 7996.
108. 4-OMs substrate exhibited a slower rate of reaction. These preliminary results suggest that the oxidative addition of ArOMs is presumably the rate-determining step. (A detailed kinetic study is currently underway).
109. We found that electron-deficient ArOMs underwent hydrolysis to form the corresponding phenols. Therefore, an anhydrous solvent is essential if electron-deficient ArOMs are used as an arylating agent.
110. M. Jalali-Heravi, M. Asadollahi-Baboli, P. Shahbazikhah, Eur. J. Med. Chem. 2008, 43, 548
111. S. M. Courtney, P. A. Hay, R. T. Buck, C. S. Colville, D. W. Porter, D. I. C. Scopes, F. C. Pollard, M. J. Page, J. M. Bennett, M. L. Hircock, E. A. McKenzie, C. R. Stubberfield, P. R. Turner, Bioorg. Med. Chem. Lett. 2004, 14, 3269.
112. M. R. Deluca, S. M. Kerwin, Tetrahedron Lett. 1997, 38, 199
113. S. Sato, T. Kajiiura, M. Noguchi, K. Takehana, T. Kobayash, T. Tsuji, J. Antibiot. 2001, 54, 102.
114. R. V. Kalla, E. Elzein, T. Perry, X. Li, V. Palle, V. Varkhedkar, A. Gimbel, T. Maa, D. Zeng, J. Zablocki, J. Med. Chem. 2006, 49, 3682
115. L. Yan, C. E. Müller, J. Med. Chem. 2004, 47, 1031
116. A. M. Hayallah, J. S. Ramrez, U. Reith, U. Schobert, B. Preiss, B. Schumacher, J. W. Daly, C. E. Müller, J. Med. Chem. 2002, 45, 1500
117. D. Zhao, W. Wang, S. Lian, F. Yang, J. Lan, J. You, Chem. Eur. J. 2009, 15, 1337.
118. D. Zhao, W. Wang, F. Yang, J. Lan, Li Yan, G. Gao, J. You, Angew. Chem. 2009, 121, 3346
119. Angew. Chem. Int. Ed. 2009, 48, 3296.
120. E. Kashiyama, I. Huchinson, M. S. Chau, S. F. Stinson, L. R. Phillips, G. Kaur, E. A. Sausville, T. D. Bradshaw, A. D. Westwell, M. F. G. Stevens, J. Med. Chem. 1999, 42, 4172
121. T. D. Bradshaw, M. F. G. Stevens, A. D. Westwell, Curr. Med. Chem. 2001, 8, 203.
122. Y. Bourne, H. C. Kolb, Z. Radic', K. B. Sharpless, P. Taylor, P. Marchot, Proc. Natl. Acad. Sci. USA 2004, 101, 1449.