Rhodium-catalyzed C-C bond formation via Heteroatom-directed C-H bond activation

Chemical Reviews

Volumn 110, Issue 2, 2010, Pages 624-655

  Colby, Denise A ^a   Bergman, Robert G ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL KETONES; C-C BOND FORMATION; C-H BOND; CH-BOND ACTIVATION; FUNCTIONALIZATIONS; HETEROATOMS; KETIMINES; KEY ISSUES; RHODIUM-CATALYZED; SELECTIVE REACTIVITY;

ALKYLATION; KETONES; OLEFINS;

RHODIUM;

CARBON; CHELATING AGENT; HETEROCYCLIC COMPOUND; RHODIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY;

ALKYLATION; CARBON; CATALYSIS; CHELATING AGENTS; HETEROCYCLIC COMPOUNDS; RHODIUM;

EID: 77349090183     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr900005n     Document Type: Article

References (230)

1. For reviews on C-H bond functionalization, see the following and leading references therein: (a) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
2. (b) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47.
3. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
4. (d) Jun, C.-H.; Moon, C. W.; Lee, H.; Lee, D.-Y. J. Mol. Catal. A 2002, 189, 145.
5. (e) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
6. (f) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 212.
7. (g) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
8. (h) Park, Y. J.; Jun, C-H. Bull. Korean Chem. Soc. 2005, 26, 871.
9. (i) Kakiuchi, F. Top. Organomet. Chem. 2007, 24, 1.
10. (j) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
11. (k) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
12. (l)Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
13. (m)Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
14. For examples of sterically driven selectivity, see: (a) Cho, J.-Y.; Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 2000, 122, 12868.
15. (b) Ishiyama, T.; Takagi, J.; Kousaku, I.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390. For examples of selectivity based on C-H acidity, see:
16. (c) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
17. (d) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066. For examples of selectivity based on electron-donating substituents, see:
18. (e) Jia, C. G.; Piao, D. G.; Oyamada, J. Z.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
19. (f) Tunge, J. A.; Foresee, L. N. Organometallics 2005, 24, 6440.
20. (g) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072.
21. (h) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
22. For examples of the application of C-H bond activation in targetoriented synthesis, see: (a) Harris, P. W. R.; Woodgate, P. D. J. Organomet. Chem. 1997, 530, 211.
23. (b) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321.
24. (c) When, P. M.; DuBois, J. J. Am. Chem. Soc. 2002, 124, 12950.
25. (d) Hinman, A.; DuBois, J. H. J. Am. Chem. Soc. 2003, 125, 11510.
26. (e) Leblanc, M.; Fagnou, K. Org. Lett. 2005, 7, 2849.
27. (f) Davies, H. M. L.; Dai, X.; Long, M. S. J. Am. Chem. Soc. 2006, 128, 2485.
28. (g) Liu, Y.; Xiao, W.; Wong, M.-K.; Che, C.-M. Org. Lett. 2007, 9, 4107. For reviews, see ref 26a and
29. (h) Godula, K.; Sames, D. Nature 2006, 312, 67.
30. (i) Lafrance, M.; Blaquiere, N.; Fagnou, K. Eur. J. Org. Chem. 2007, 811.
31. (j)Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
32. (a) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem.-Eur. J. 2002, 8, 2423.
33. (b) Kakiuchi, F.; Ohtaki, H.; Sonoda, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 918.
34. (c) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616.
35. (d) Matsubara, T.; Koga, N.; Musaev, D.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692.
36. (e) Matsubara, T.; Koga, N.; Musaev, D.; Morokuma, K. Organomertallics 2000, 19, 2318.
37. (f) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am Chem. Soc. 2008, 130, 3645.
38. (a) Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267.
39. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201.
40. (c) Lim, Y.-G.; Kang, J.-B. Bull. Korean Chem. Soc. 1997, 18, 1213.
41. (d) Lim, Y.-G.; Han, J.-S.; Kang, J.-B. Bull. Korean Chem. Soc. 1998, 19, 1143.
42. (e) Lim, Y.-G.; Han, J.-S.; Koo, B.-T.; Kang, J.-B. Bull. Korean Chem. Soc. 1999, 20, 1097.
43. (f) Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K. Y. Angew. Chem., Int. Ed. 2000, 39, 3440.
44. For examples of chelation-assisted ortho-functionalization of aryl imines under Re catalysis, see the following and references therein: (a) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.
45. (b) Kuninobu, Y.; Kikuchi, K.; Tokunaga, Y.; Nishina, Y.; Takai, K. Tetrahedron 2008, 64, 5974.
46. (a) Jo, E.-A.; Cho, E.-G.; Jun, C.-H. Synlett 2007, 1059. For an example using 2-vinylpyridines to functionalize polybutadiene, see:
47. (b) Lim, Y.-G.; Han, J.-S.; Koo, B. T.; Kang, J.-B. Polymer 2000, 41, 4351.
48. (a) See ref 6a. Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem-Eur. J. 2002, 8, 2423. For further examples of chelation-assisted hydroacylation, see the following and references therein.
49. (b) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200.
50. (c) Jun, C.-H.; Hong, J.-B.; Lee, D.-Y. Synlett 1999, 1.
51. (d) Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070.
52. (e) Jun, C.-H.; Lee, H.; Hong, J.-B.; Kwon, B.-I. Angew. Chem., Int. Ed. 2002, 41, 2146.
53. (f) Jun, C.-H.; Moon, C. W.; Lim, S.-G.; Lee, H. Org. Lett. 2002, 4, 1595.
54. (g) Jun, C.-H.; Lee, J. H. Pure Appl. Chem. 2004, 76, 577.
55. (h) Jo, E.-A.; Jun, C.-H. Eur. J. Org. Chem. 2006, 2504.
56. Jun, C.-H.; Chung, K.-Y.; Hong, J.-B. Org. Lett. 2001, 3, 785.
57. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687.
58. Vo-Thanh, G.; Lahrache, H.; Loupy, A.; Kim, I.-J.; Chang, D.-H.; Jun, C.-H. Tetrahedron 2004, 60, 5539.
59. Jo, E.-A.; Ahn, J.-A.; Jun, C.-H. Bull. Korean Chem. Soc. 2007, 28, 2020.
60. (a) Yoon, J. H.; Park, Y. J.; Lee, J. H.; Yoo, J.; Jun, C-.H. Org. Lett. 2005, 7, 2889. For chelation-assisted hydroarylation, see:
61. (b) Kim, D.-W.; Lim, S.-G.; Jun, C.-H. Org. Lett. 2006, 8, 2937.
62. (c) Chang, D.-H.; Lee, D.-Y.; Hong, B.-S.; Choi, J.-H.; Jun, C.-H. J. Am. Chem. Soc. 2004, 126, 424. For use in hydroacylation reactions, see:
63. (d) Park, J.-W.; Park, J.-H.; Jun, C.-H. J. Org. Chem. 2008, 73, 5598. For a review on recyclable catalysts for C-H activation, see:
64. (e) Park, Y. J.; Park, J.-W.; Jun, C.-H. Ace Chem. Res. 2008, 41, 222.
65. (a) Kakiuchi, F.; Sato, T.; Igi, K.; Chatani, N.; Murai, S. Chem. Lett. 2001, 386. For leading references on the use of aldehydes in hydroacylation reactions, see the following:
66. (b) Jun, C.-H.; Jo, E.A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869.
67. (c) Dempsey Hyatt, I. F.; Anderson, H. K.; Morehead, A. T.; Sargent, A. L. Organometallics 2008, 27, 135.
68. (d) Jun, C.-H.; Park. Y. J. Handbook of C-H Transformations 2005, 1, 303.
69. (e) Bosnich, B. Acc. Chem. Res. 1998, 31, 667.
70. (f) Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. Org. Lett. 2003, 5, 1365.
71. (g) Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144.
72. (h) Tanaka, K.; Tanaka, M.; Suemune, H. Tetrahedron Lett. 2005, 46, 6053.
73. (i) Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916.
74. (j) Shimizu, M.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Asian J. 2008, 3, 881.
75. (a) Lim, Y.-G.; Han, J.-S.; Koo, B. T.; Kang, J.-B. J. Mol. Catal. A 2004, 41.
76. (b) Lim, Y.-G.; Han, J.-S.; Yang, S.-S.; Chun, J. H. Tetrahedron Lett. 2001, 42, 4853.
77. Lim, Y.-G.; Koo, B. T. Tetrahedron Lett. 2005, 46, 7997.
78. (a) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2005, 70, 6775.
79. (b) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692.
80. Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301.
81. An efficient synthesis of 33 via a tandem aryl alkylation/Heck coupling sequence was recently reported: (a) Alberico, D.; Rudolph, A.; Lautens, M. J. Org. Chem. 2007, 72, 775.
82. (b) Alberico, D.; Lautens, M. Synlett 2006, 2969.
83. (a) O'Malley, S. J.; Tan, K. L.; Watzke, A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 13496.
84. (b) Watzke, A.; O'Malley, S. J.; Bergman, R. G.; Ellman, J. A. J. Nat. Prod. 2006, 69, 1231.
85. Watzke, A.; Wilson, R. M.; O'Malley, S. J.; Bergman, R. G.; Ellman, J. A. Synlett 2007, 2283.
86. For enantioselective carbenoid and nitrenoid insertions, see the following and references therein: (a) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417. For an example of an atropselective alkylation, see:
87. (b) Kakiuchi, F.; Le Gendre, P.; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron: Asymmetry 2000, 11, 2647; see also ref 18e.
88. (c) Bosnich, B.; Wang, X. Organometallics 1994, 13, 4131.
89. (d) Han, X.; Widenhoefer, R. A. Org. Lett. 2006, 8, 3801.
90. (e) Shi, B.F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
91. (a) Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425.
92. (b) Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1998, 71, 285.
93. (a) Harada, H.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2008, 73, 6772.
94. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
95. Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2006, 8, 1745.
96. See the following and references therein: (a) Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405.
97. (b) Ito, J.-i.; Kitase, M.; Nishiyama, H. Organometallics 2007, 26, 6412.
98. For early examples of the Rh-catalyzed coupling of benzene and azobenzenes with alkynes, see the following:(a) Hong, P.; Cho, B.R.; Yamazaki, H. Chem. Lett. 1980, 507.
99. (b) Yamazaki, H.; Hong, P. J. Mol. Catal. A 1983, 21, 133.
100. (c) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385.
101. (d) Dürr, U.; Kisch, H. Synlett 1997, 1335.
102. Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 7609.
103. Katagiri, T.; Mukai, T.; Satoh, T.; Hirano, K.; Miura, M. Chem. Lett. 2009, 38, 118.
104. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C-H. Org. Lett. 2003, 5, 2759.
105. (a) Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362.
106. (b) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407.
107. For a discussion of the mechanism of ortho-C-H bond activation in a related Rh-benzoate complex, see the following and references therein: Kisenyi, J. M.; Sunley, G. J.; Cabeza, J. A.; Smith, A. J.; Adams, H.; Salt, N. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2459.
108. Tanaka, K.; Otake, Y.; Wada, A.; Noguchi, K.; Hirano, M. Org. Lett. 2007, 9, 2203.
109. Tsuchikama, K.; Kuwata, Y.; Tahara, Y.-k.; Yoshinami, Y.; Shibata, T. Org. Lett. 2007, 9, 3097.
110. Tanaka, K.; Otake, Y.; Sagai, H.; Noguchi, K.; Hirano, M. Angew. Chem., Int. Ed. 2008, 47, 1312.
111. For examples of chelation-assisted arylation methods by Ru or Pd catalysis, see ref 1j as well as the following and leading references therein: (a) Oi, S.; Funayama, R.; Hattori, T.; Inoue, Y. Tetrahedron 2008, 64, 6051.
112. (b) Ackermann, L.; Althammer, A.; Born, R. Tetrahedron 2008, 64, 6115.
113. (c) Shabashov, D.; Molina Maldonado, M.; Daugulis, O. J. Org. Chem. 2008, 73, 7818.
114. (d) Lafrance, M.; Lapointe, D.; Fagnou, K. Tetrahedron 2008, 64, 6015.
115. (e) Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949.
116. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
117. (g) Ackermann, L. Top. Organomet. Chem. 2007, 24, 35.
118. Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439.
119. Zhao, X.; Yu, Z. J. Am. Chem. Soc. 2008, 130, 8136.
120. Vogler, T.; Studer, A. Org. Lett. 2008, 10, 129.
121. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
122. Miyamura, S.; Tsurugi, H.; Satoh, T.; Miura, M. J. Organomet. Chem. 2008, 693, 2438.
123. For a detailed study on Rh(I) phosphinite complexes and their alkylation chemistry, see: (a) Lewis, J. C.; Wu, J.; Bergman, R. G.; Ellman, J. A. Organometallics 2005, 24, 5737. For early examples using Ru, see:
124. (b) Lewis, L. N. Inorg. Chem. 1985, 24, 4433.
125. (c) Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728.
126. (a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
127. (b) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
128. Oi, S.; Watanabe, S.-i.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003, 44, 8665.
129. For examples of Ru-catalyzed C-H carbonylations, see ref 1c and references therein. See also: (a) Chatani, N.; Yorimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002, 67, 7557.
130. (b) Asaumi, T.; Chatani, N.; Matsuo, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2003, 68, 7538.
131. (a) Ishii, Y.; Chatani, N.; Kakiuchi, F.; Murai, S. Organometallics 1997, 16, 3615.
132. (b) Ishii, Y.; Chatani, N.; Kakiuchi, F.; Murai, S. Tetrahedron Lett. 1997, 38, 7565.
133. (c) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129.
134. (d) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
135. Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
136. Chatani, N.; Uemura, T.; Asaumi, T.; Ie, Y.; Kakiuchi, F.; Murai, S. Can. J. Chem. 2005, 83, 755.
137. Guan, Z.-H.; Ren, Z.-H.; Spinella, S. M.; Yu, S.; Liang, Y.-M.; Zhang, X. J. Am. Chem. Soc. 2009, 131, 729.
138. Early examples using Ru showed limited substrate scope: (a) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5317.
139. (b) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679.
140. (c) Sato, T.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1998, 893.
141. (d) Kakiuchi, F.; Sato, T.; Igi, K.; Chatani, N.; Murai, S. Chem. Lett. 2001, 386.
142. (a) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Commun. 1996, 585.
143. (b) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1998, 699.
144. (c) Lim, Y.-G.; Kang, J.-B.; Koo, B. T. Tetrahedron Lett. 1999, 40, 7691.
145. Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836.
146. Jun, C.-H.; Moon, C. W.; Kim, Y.-M.; Lee, H.; Lee, J. H. Tetrahedron Lett. 2002, 43, 4233.
147. For an early example where a 2-pyridylallylamine underwent preferential imine C-H alkylation over olefinic C-H alkylation, see: Jun, C.-H.; Lee, H.; Park, J.-B.; Lee, D.-Y. Org. Lett. 1999, 1, 2161.
148. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am Chem. Soc. 2006, 128, 5604.
149. Tsai, A. S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6316.
150. The first enantioselective synthesis of 132 also utilized this disconnection: Ichikawa, M.; Takahashi, M.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2004, 126, 16553.
151. Cao, C.; Li, Y.; Shi, Y.; Odom, A. L. Chem. Commun. 2004, 2002.
152. Hoops, S.; Sahle, S.; Gauges, R.; Lee, C.; Pahle, J.; Simus, N.; Singhal, M.; Xu, L.; Mendes, P.; Kummer, U. Bioinformatics 2006, 22, 3067. See also: http://www.copasi.org/tiki-index.php.
153. For recent reviews on pyridine synthesis, see: (a) Varela, J.; Saa, C. Chem. Rev. 2003, 103, 3787.
154. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
155. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325.
156. For examples of intramolecular cyclizations of enynes that are speculated to proceed via [4 + 2] cycloadditions, see: Saito, A.; Hironaga, M.; Oda, S.; Hanzawa, Y. Tetrahedron Lett. 2007, 48, 6852.
157. Yotphan, S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2452.
158. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
159. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685.
160. For a review on the synthesis of 2-substituted azoles, see: (a) Zificsak, C A.; Hlasta, D. J. Tetrahedron 2004, 60, 8991. For an example of Ir-catalyzed alkylation of azoles with aldehydes, see:
161. (b) Fukumoto, Y.; Sawada, K.; Hagihara, M.; Chatani, N.; Murai, S. Angew. Chem., Int. Ed. 2002, 41, 2779. For acylation using Ru, see:
162. (c) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc 1996, 118, 493.
163. (d) Moore, E. J.; Pretzer, W. R.; O'Connel, T. J.; Harris, J.; LaBounty, L.; Cou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. For Ni- and Pd-based alkylations of N-heterocyclic carbenes, see the following and references therein.
164. (e) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845.
165. (f) Normand, A. T.; Hawkes, K. J.; Clement, N. D.; Cavell, K. J.; Yates, B. F. Organometallics 2007, 26, 5352.
166. (g) Normand, A. T.; Yen, S. K.; Huynh, H. V.; Hore, T. S. A.; Cavell, K. J. Organometallics 2008, 27, 3153.
167. (h) Cavell, K. J. Dalton Trans. 2008, 6676.
168. Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131.
169. Rech, J. C.; Yato, M.; Duckett, D.; Ember, B.; LoGrasso, P. V.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 490.
170. Graczyk, P. P.; Khan, A.; Bhatia, G. S.; Palmer, V.; Medland, D.; Numata, H.; Oinuma, H.; Catchick, J.; Dunne, A.; Ellis, M.; Smales, C.; Whitfield, J.; Neame, S. J.; Shah, B.; Wilton, D.; Morgan, L.; Patel, T.; Chung, R.; Desmond, H.; Staddon, J. M.; Sato, N.; Inoue, A. Bioorg. Med. Chem. Lett. 2005, 15, 4666.
171. (a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
172. (b) Tan, K. L.; Park, S.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2004, 69, 7329.
173. Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 1685.
174. Wiedemann, S. H.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2006, 71, 1969.
175. "Phoban" is commercially available as a technical mixture of [3.3.1] and [4.2.1] isomers. For the separation of isomers, see: Downing, J. H.; Gee, V.; Pringe, P. G. Chem. Commun. 1997, 1527.
176. This method was also used by Stevens and Nakagawa in their synthesis of vasicoline: Nakagawa, Y.; Stevens, R. V. J. Org. Chem. 1988, 53, 1873.
177. (a) Alvarez, E.; Conejero, S.; Paneque, M.; Petronilho, A.; Poveda, M. L.; Serrano, O.; Carmona, E. J. Am. Chem. Soc. 2006, 128, 13060.
178. (b) Esteruelas, M. A.; Fernandez-Alvarez, F. J.; Onate, E. J. Am. Chem. Soc. 2006, 128, 13044.
179. (c) Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. J. Organomet. Chem. 2004, 689, 3857.
180. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
181. For examples of pyridine alkylation using early metals, see the following and references therein: (a) Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778.
182. (b) Rodewald, S.; Jordan, R. F. J. Am. Chem. Soc. 1994, 116, 4491.
183. (c) Diaconescu, P. L. Curr. Org. Chem. 2008, 12, 1388. For Ru-catalyzed alkenylation of pyridine, see:
184. (d) Murakami, M.; Hori, S. J. Am. Chem. Soc. 2003, 125, 4720.
185. Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202.
186. (a) Crabtree, R. H. Dalton 2001, 2437.
187. (b) Bercaw, J. E.; Labinger, J. A. Nature 2002, 417, 507.
188. (c) Bergman, R. G. Nature 2007, 446, 391.
189. The synthesis and reactivity of NHC complexes is explored in the following and references therein: (a) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122.
190. (b) Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247.
191. (c) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
192. Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
193. Wiedemann, S. H.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 2452.
194. Gribble, M.; Ellman, J. A.; Bergman, R. G. Organometallics 2008, 27, 2152.
195. For uncatalyzed and proton-catalyzed 1,2-hydrogen shifts at imidazol2-yl carbenes, see: (a) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
196. (b) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
197. For computational studies on the oxidative addition of 1,3-dimethylimidazolium salts to Rh and Ir complexes, see: (a) Hawkes, K. J.; McGuinness, D. S.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2004, 2505.
198. (b) Appelhans, L. N.; Zuccaccia, D.; Kovacevic, A.; Chianese, A. R.; Miecznikowski, J. R.; Macchioni, A.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 16299.
199. (a) Hawkes, K. J.; Cavell, K. J.; Yates, B. F. Organometallics 2008, 27, 4758.
200. (b) See also refs 89a and 70e-h.
201. (a) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12.
202. (b) See also refs 84c and 88b.
203. See the following and leading references therein: (a) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
204. (b) Miura, M.; Satoh, T. Top. Organomet. Chem. 2005, 14, 55.
205. (c) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.; Lazareva, A. Synlett 2006, 3382.
206. (d) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
207. (e) Touré, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979.
208. (f) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
209. (g) Storr, T. E.; Firth, A. G.; Wilson, K.; Darley, K.; Baumann, C. G.; Fairlamb, I. J. S. Tetrahedron 2008, 64, 6125.
210. (h) Derridj, F.; Djebbar, S.; BenaliBaitich, O.; Doucet, H. J. Organomet. Chem. 2008, 693, 135.
211. (i) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
212. (J) Kondo, Y.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111.
213. (k) See also refs 1j, 40d,f,g, and 70a.
214. (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
215. (b) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
216. (c) Yotphan, S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 1511.
217. Lewis, J. C.; Wiedemann, S. H.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35.
218. For a review on hydrodehalogenation, see: Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009.
219. Similar reactivity was previously observed: Christ, M. L.; SaboEtienne, S.; Chaudret, B. Organometallics 1995, 14, 1082, and references therein.
220. Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1585.
221. Lewis, J. C.; Berman, A. M.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2493.
222. Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
223. A similar dependence on pivalate counterions has been observed for Pd systems. See ref 40d.
224. (a) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
225. (b) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. Tetrahedron 2008, 64, 6073.
226. For an example of a general cross-coupling method, see: Billingsley, K. L.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 4695.
227. The direct ortho-arylation of pyridine N-oxides has been reported using Pd: (a) Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
228. (b) Leclerc, J.-P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
229. (c) Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254. The direct ortho-arylation of N-iminopyridinium ylides has also been reported: Larivee, A.; Mousseau, J. J.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 52.
230. Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.