Robust ruthenium(II)-catalyzed C-H arylations: Carboxylate assistance for the efficient synthesis of angiotensin-II-receptor blockers

Organic Process Research and Development

Volumn 19, Issue 1, 2015, Pages 260-269

  Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CATALYSTS; CHEMICAL REACTIONS; RUTHENIUM;

ANGIOTENSIN II; ARYLATIONS; BI-FUNCTIONAL; CATALYST LOADINGS; EFFICIENT SYNTHESIS; FUNCTIONALIZATIONS; ORGANIC HALIDES; RUTHENIUM COMPLEXES;

RUTHENIUM COMPOUNDS;

EID: 84921367891     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op500330g     Document Type: Review

References (175)

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062-5085
2. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710
3. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
4. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563-639
5. Modern Crop Protection Compounds, 2 nd ed., Vols. 1-3; Krämer, W.; Schirmer, U.; Jeschke, P.; Witschel, M., Eds.; Wiley-VCH: Weinheim, 2011.
6. Han, J.; Chang, X.-Y.; Zhu, L.-R.; Pang, M.-L.; Meng, J.-B.; Chui, S.-Y.; Lai, S.-W.; Roy, V. A. L. Chem.-Asian J. 2009, 4, 1099-1107
7. Baudoin, O.; Guéritte, F. Natural bridged biaryls with axial chirality and antimitotic properties. In Studies in natural product chemistry, Vol. 29; Ur-Rahman, A., Ed.; Elsevier: Amsterdam, 1996; pp 355-418.
8. Bringmann, G.; Menche, D. Acc. Chem. Res. 2001, 34, 615-624
9. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V. Handbook of Liquid Crystals Set, Vol. 1; Wiley-VCH: Weinheim, 1998.
10. Solladié, G.; Zimmermann, R. G. Angew. Chem., Int. Ed. Engl. 1984, 23, 348-362
11. Gray, G. W.; Luckhurst, G. R. The molecular physics of liquid crystal; Academic Press: New York, 1979, and references cited therein.
12. Larock, R. C. Comprehensive Organic Transformations, 2 nd ed.; Wiley-VCH: Weinheim, 1999.
13. Aldemir, H.; Richarz, R.; Gulder, T. A. M. Angew. Chem., Int. Ed. 2014, 53, 8286-8293
14. Ackermann, L. Modern Arylation Methods; Wiley-VCH: Weinheim, 2009.
15. Tsuji, J. Palladium Reagents and Catalysts, 2 nd ed.; Wiley: Chichester, 2004.
16. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, 2 nd ed.; Wiley-VCH: Weinheim, 2004.
17. Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A.; Bräse, S.; Oestreich, M., Eds.; Wiley-VCH: Weinheim, 2014.
18. Majumdar, K. C.; Sinha, B. Synthesis 2013, 45, 1271-1299
19. Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485-496
20. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347
21. Shen, H. C. In Applications of Transition Metal Catalysis in Drug Discovery and Development; Crawley, M. L.; Trost, B. M., Eds.; John Wiley&Sons, Inc.: Hoboken, NJ, 2012; pp 25-95.
22. Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N. Beilstein J. Org. Chem. 2011, 7, 442-495
23. Cooper, T. W. J.; Campbell, I. B.; Macdonald, S. J. F. Angew. Chem., Int. Ed. 2010, 49, 8082-8091
24. Federsel, H.-J. Acc. Chem. Res. 2009, 42, 671-680
25. Budarin, V. L.; Shuttleworth, P. S.; Clark, J. H.; Luque, R. Curr. Org. Synth. 2010, 7, 614-627
26. Slagt, V. F.; de Vries, A. H. M.; de Vries, J. G.; Kellogg, R. M. Org. Process Res. Dev. 2010, 14, 30-47
27. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854-2867
28. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Soc. 2008, 41, 40-49
29. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705
30. Littke, A. F. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009; pp 25-68.
31. Mesganaw, T.; Ellman, J. A. Org. Process Res. Dev. 2014, 18, 1097-1104
32. Ackermann, L. J. Org. Chem. 2014, 79, 8948-8954
33. Tani, S.; Uehara, T. N.; Yamaguchi, J.; Itami, K. Chem. Sci. 2014, 5, 123-135
34. Tsurugi, H.; Yamamoto, K.; Nagae, H.; Kaneko, H.; Mashima, K. Dalton Trans. 2014, 43, 2331-2343
35. Rossi, R.; Bellina, F.; Lessi, M.; Manzini, C. Adv. Synth. Catal. 2014, 356, 17-117
36. Kakiuchi, F.; Kochi, T.; Murai, S. Synlett 2014, 25, 2390-2414
37. Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208-1219
38. Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74-100
39. De Sarkar, S.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461-1479
40. Zhang, X.-S.; Chen, K.; Shi, Z.-J. Chem. Sci. 2014, 5, 2146-2159
41. Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369-375
42. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726-11743
43. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960-9009
44. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
45. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177-185
46. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885-1898
47. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902-4911
48. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212-11222
49. Daugulis, O. Top. Curr. Chem. 2010, 292, 57-84
50. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013-1025
51. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238
52. Bergman, R. G. Nature 2007, 446, 391-393 and references cited therein
53. Ackermann, L.; Vicente, R.; Kapdi, A. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
54. Ackermann, L.; Kapdi, A. R.; Potukuchi, H. K.; Kozhushkov, S. I. Syntheses via C-H Bond Functionalizations. In Handbook of Green Chemistry, Li, C.-J., Ed.; Wiley-VCH: Weinheim, 2012; pp 259-305.
55. Dyker, G. Handbook of C-H Transformations, Wiley-VCH: Weinheim, 2005.
56. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-162
57. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
58. Satoh, T.; Miura, M. Top. Organomet. Chem. 2007, 24, 61-84
59. Ackermann, L. Top. Organomet. Chem. 2007, 24, 35-60
60. Omae, I. Coord. Chem. Rev. 2004, 248, 995-1023
61. See also: Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236-10254
62. Kim, J. H.; Lee, J. H.; Paik, S. H.; Kim, J. H.; Chi, Y. H. Arch. Pharm. Res. 2012, 35, 1123-1126
63. De Catarina, A. R.; Harper, A. R.; Cuculi, F. Vasc. Health. Risk. Manag. 2012, 8, 299-305 and references cited therein
64. Bühlmayer, P.; Furet, P.; Criscione, L.; de Gasparo, M.; Whitebread, S. I.; Schmidlin, T.; Lattmann, R.; Wood, J. Bioorg. Med. Chem. Lett. 1994, 4, 29-34
65. Chang, L. L.; Ashton, W. T.; Flanagan, K. L.; Chen, T.-B.; O'Malley, S. S.; Zingaro, G. J.; Kivlighn, S. D.; Siegl, P. K. S.; Lotti, V. J.; Chang, R. S. L.; Greenlee, W. J. J. Med. Chem. 1995, 38, 3741-3758
66. Kubo, K.; Kohara, Y.; Inada, Y.; Shibouta, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. J. Med. Chem. 1993, 36, 2343-2349
67. Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Johnson, A. L.; Price, W. A.; Wells, G. J.; Wong, P. C.; Calabrese, J. C.; Timmermans, P. B. M. W. M. J. Med. Chem. 1990, 33, 1312-1329
68. Zhou, L.; Lu, W. Chem.-Eur. J. 2014, 20, 634-642
69. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083
70. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
71. Scheuermann, C. J. Chem.-Asian J. 2010, 5, 436-451
72. Wu, Z.; Luo, F.; Chen, S.; Li, Z.; Xiang, H.; Zhou, X. Chem. Commun. 2013, 49, 7653-7655
73. Liu, W.; Ackermann, L. Org. Lett. 2013, 15, 3484-3486
74. Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 458-462
75. Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 13864-13867 and references cited therein
76. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879-5918
77. Ackermann, L. Chem. Commun. 2010, 46, 4866-4877 and references cited therein
78. Kakiuchi, F.; Chatani, N. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, 2004; pp 219-255.
79. Ackermann, L. Pure Appl. Chem. 2010, 82, 1403-1413
80. Ackermann, L. Synlett 2007, 507-526
81. Ackermann, L.; Born, R.; Spatz, J. H.; Althammer, A.; Gschrei, C. J. Pure Appl. Chem. 2006, 78, 209-214
82. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639
83. de Mendoza, P.; Echavarren, A. M., In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009.
84. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
85. Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728-2735
86. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531
87. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834
88. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5820-5831
89. Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Giardiello, M.; Hilton, S. T.; Russell, D. R. Dalton Trans. 2003, 4132-4138
90. Fabre, I.; von Wolff, N.; Le Duc, G.; Ferrer Flegeau, E.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. Chem.-Eur. J. 2013, 19, 7595-7604
91. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345
92. Ackermann, L. Acc. Chem. Res. 2014, 47, 281-295
93. Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y. Chem. Lett. 2008, 37, 994-995
94. Oi, S.; Aizawa, E.; Ogino, Y.; Inoue, Y. J. Org. Chem. 2005, 70, 3113-3119
95. Ouellet, S. G.; Roy, A.; Molinaro, C.; Angelaud, R.; Marcoux, J.-F.; O'Shea, P. D.; Davies, I. W. J. Org. Chem. 2011, 76, 1436-1439
96. Seki, M. RSC Adv. 2014, 4, 29131-29133
97. A very recent related sulfonate-assisted direct arylation: Seki, M. ACS Catal. 2014, 4, 4047-4050
98. Ackermann, L.; Vicente, R. Top. Curr. Chem. 2010, 292, 211-229
99. Ackermann, L. Isr. J. Chem. 2010, 50, 652-663
100. Ackermann, L. Synthesis 2006, 1557-1571
101. Ackermann, L. Org. Lett. 2005, 7, 3123-3126
102. Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619-2622
103. Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299-2302
104. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032-5035
105. Ackermann, L.; Potukuchi, H. K. Org. Biomol. Chem. 2010, 8, 4503-4513
106. Astruc, D.; Liang, L.; Rapakousiou, A.; Ruiz, J. Acc. Chem. Res. 2012, 45, 630-640
107. Agalave, S. G.; Maujan, S. R.; Pore, V. S. Chem.-Asian J. 2011, 6, 2696-2718
108. Pedersen, D. S.; Abell, A. Eur. J. Org. Chem. 2011, 2399-2411
109. Hanni, K. D.; Leigh, D. A. Chem. Soc. Rev. 2010, 39, 1240-1251
110. Kappe, C. O.; Van der Eycken, E. Chem. Soc. Rev. 2010, 39, 1280-1290
111. El-Sagheer, A. H.; Brown, T. Chem. Soc. Rev. 2010, 39, 1388-1405
112. Qin, A.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2010, 2522-2544
113. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015
114. Nandivada, H.; Jiang, X.; Lahann, J. Adv. Mater. 2007, 19, 2197-2208
115. Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674-1689
116. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369-1380
117. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262
118. Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025
119. Dondoni, A. Chem.-Asian J. 2007, 2, 700-708
120. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137 and references cited therein.
121. Ackermann, L.; Mulzer, M. Org. Lett. 2008, 10, 5043-5045
122. Ackermann, L.; Lygin, A. V. Org. Lett. 2011, 13, 3332-3335
123. Ackermann, L.; Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154-1157
124. Zhang, F.; Spring, D. R. Chem. Soc. Rev. 2014, 43, 6894-6905
125. Wang, C.; Huang, Y. Synlett 2013, 24, 145-149
126. Li, B.; Darcel, C.; Dixneuf, P. H. ChemCatChem 2014, 6, 127-130
127. Al Mamari, H. H.; Diers, E.; Ackermann, L. Chem.-Eur. J. 2014, 20, 9739-9743
128. Zhao, Y.; Snieckus, V. Adv. Synth. Catal. 2014, 356, 1527-1532
129. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2010, 49, 6629-6632
130. Ackermann, L.; Pospech, J.; Potukuchi, H. K. Org. Lett. 2012, 14, 2146-2149
131. Ackermann, L. Chem. Commun. 2010, 46, 4866-4877
132. Ackermann, L.; Novák, P.; Vicente, R.; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48, 6045-6048
133. Schinkel, M.; Marek, I.; Ackermann, L. Angew. Chem., Int. Ed. 2013, 52, 3977-3980
134. Hofmann, N.; Ackermann, L. J. Am. Chem. Soc. 2013, 135, 5877-5884
135. Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50, 6379-6382
136. For notable mechanistic studies: Li, B.; Feng, H.; Wang, N.; Ma, J.; Song, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2012, 18, 12873-12879
137. Nakanowatari, S.; Ackermann, L. Chem.-Eur. J. 2014, 20, 5409-5413
138. Ma, C.; Ai, C.; Li, Z.; Li, B.; Song, H.; Xu, S.; Wang, B. Organometallics 2014, 33, 5164-5172
139. Suzuki, C.; Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2014, 356, 1521-1526
140. Ogiwara, Y.; Tamura, M.; Kochi, T.; Matsuura, Y.; Chatani, N.; Kakiuchi, F. Organometallics 2014, 33, 402-420
141. Mehta, V. P.; Garcia-Lopez, J.-A.; Greaney, M. F. Angew. Chem., Int. Ed. 2014, 53, 1529-1533
142. Li, J.; John, M.; Ackermann, L. Chem.-Eur. J. 2014, 20, 5403-5408
143. Kornhaaß, C.; Kuper, C.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1619-1624
144. Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. J. Org. Chem. 2014, 79, 6123-6134
145. Li, J.; Ackermann, L. Tetrahedron 2014, 70, 3342-3348
146. Nan, J.; Zuo, Z.; Luo, L.; Bai, L.; Zheng, H.; Yuan, Y.; Liu, J.; Luan, X.; Wang, Y. J. Am. Chem. Soc. 2013, 135, 17306-17309
147. Reddy, M. C.; Manikandan, R.; Jeganmohan, M. Chem. Commun. 2013, 49, 6060-6062
148. Dooley, J. D.; Chidipudi, S. R.; Lam, H. W. J. Am. Chem. Soc. 2013, 135, 10829-10836
149. Wang, L.; Ackermann, L. Org. Lett. 2013, 15, 176-179
150. Zhang, J.; Ugrinov, A.; Zhao, P. Angew. Chem., Int. Ed. 2013, 52, 6681-6684
151. Villuendas, P.; Urriolabeitia, E. P. J. Org. Chem. 2013, 78, 5254-5263
152. Deponti, M.; Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Org. Biomol. Chem. 2013, 11, 142-148
153. Ma, W.; Graczyk, K.; Ackermann, L. Org. Lett. 2012, 14, 6318-6321
154. Parthasarathy, K.; Senthilkumar, N.; Jayakumar, J.; Cheng, C.-H. Org. Lett. 2012, 14, 3478-3481
155. Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2012, 48, 2030-2032
156. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764-767
157. Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 706-708
158. and reference 66.
159. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 4, 886-896
160. Dastbaravardeh, N.; Schnürch, M.; Mihovilovic, M. D. Eur. J. Org. Chem. 2013, 2878-2890
161. Kumar, N. Y. P.; Jeyachandran, R.; Ackermann, L. J. Org. Chem. 2013, 78, 4145-4152
162. Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem. Commun. 2014, 50, 29-39
163. Yang, F.; Rauch, K.; Kettelhoit, K.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 11285-11288
164. Yang, X.; Sun, Y.; Chen, Z.; Rao, Y. Adv. Synth. Catal. 2014, 356, 1625-1630
165. Wang, L.; Ackermann, L. Chem. Commun. 2014, 50, 1083-1085
166. Liu, W.; Ackermann, L. Chem. Commun. 2014, 50, 1878-1881
167. Diers, E.; Kumar, N. Y. P.; Mejuch, T.; Marek, I.; Ackermann, L. Tetrahedron 2013, 69, 4445-4453
168. Diers, E. Dissertation, Georg-August-Universität Göttingen, 2013.
169. These findings were first disclosed at the 4th International Symposium on Advances in Synthetic and Medicinal Chemistry (ASMC) in St. Petersburg on Aug 25, 2011.
170. Seki, M. ACS Catal. 2011, 1, 607-610
171. Seki, M.; Nagahama, M. J. Org. Chem. 2011, 76, 10198-10206
172. Seki, M. Synthesis 2012, 3231-3237
173. Ackermann, L.; Novák, P.; Vicente, R.; Pirovano, V.; Potukuchi, H. K. Synthesis 2010, 2245-2253
174. Ashby, E. C. Acc. Chem. Res. 1988, 21, 414-421
175. Collins, K. D.; Gensch, T.; Glorius, F. Nat. Chem. 2014, 6, 859-871