α-alkylation of ketones with primary alcohols catalyzed by a Cp∗Ir complex bearing a functional bipyridonate ligand

Journal of Organic Chemistry

Volumn 79, Issue 21, 2014, Pages 10447-10455

  Li, Feng ^a   Ma, Juan ^a   Wang, Nana ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYST ACTIVITY; IRIDIUM; KETONES;

AIR ATMOSPHERE; C-C BOND FORMING REACTION; CARBONYL GROUPS; ELECTROPHILES; ENVIRONMENTALLY BENIGN; HYDROGEN TRANSFER; PRIMARY ALCOHOLS; TERT-AMYL ALCOHOLS;

LIGANDS;

1 INDANONE; 2 PROPANOL; ACETOPHENONE; ACETOPHENONE DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ANILINE; BENZALDEHYDE; BENZYL ALCOHOL; BUTANOL; CARBONYL DERIVATIVE; CYCLOHEXYLMETHANOL; HEXANOL; HYDROGEN; IRIDIUM COMPLEX; KETONE DERIVATIVE; LIGAND; METHANOL; ORGANOMETALLIC COMPOUND; PENTANOL; PROPIOPHENONE DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG; 2,2' BIPYRIDINE; COORDINATION COMPOUND; IRIDIUM; KETONE;

AIR; AIR ATMOSPHERE; ALDOL REACTION; ALKYLATION; ALPHA ALKYLATION; ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL BOND; CROSS ALDOL CONDENSATION; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION;

2,2'-DIPYRIDYL; ALCOHOLS; ALKYLATION; CATALYSIS; COORDINATION COMPLEXES; IRIDIUM; KETONES; LIGANDS; METHYLATION; MOLECULAR STRUCTURE;

EID: 84909992896     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502051d     Document Type: Article

References (103)

1. Caine, D. In. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 1-63.
2. Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
3. Guillena, G.; Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358-2364
4. Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555-1575
5. Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans. 2009, 753-765
6. Dobereiner, G. E.; Grabtree, R. H. Chem. Rev. 2010, 110, 681-703
7. Guillena, G.; Ramon, D.; Yus, M. Chem. Rev. 2010, 110, 1611-1641
8. Suzuki, T. Chem. Rev. 2011, 111, 1825-1845
9. Bahn, S.; Imm, S.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 1853-1864
10. Marr, A. C. Catal. Sci. Technol. 2012, 2, 279-287
11. Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704-712
12. Cho, C. S.; Kim, B. T.; Kim, T. J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020-9022
13. Cho, C. S.; Kim, B. T.; Kim, T. J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987-7989
14. Martínez, R.; Brand, G. J.; Ramon, D. J.; Yus, M. Tetrahedron Lett. 2005, 46, 3683-3686
15. Martínez, R.; Ramon, D. J.; Yus, M. Tetrahedron 2006, 62, 8988-9001
16. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72-73
17. Onodera, G.; Nishibayashi, Y.; Uemura, S. Angew. Chem., Int. Ed. 2006, 45, 3819-3822
18. Morita, M.; Obora, Y.; Ishii, Y. Chem. Commun. 2007, 2850-2852
19. Rueping, M.; Phapale, V. B. Green Chem. 2012, 14, 55-57
20. Bhat, S.; Sridharan, V. Chem. Commun. 2012, 48, 4701-4703
21. Kwon, M. S.; Kim, N.; Seo, S. H.; Park, I. S.; Cheedrala, R. K.; Park, J. Angew. Chem., Int. Ed. 2005, 44, 6913-6915
22. Cho, C. S. J. Mol. Catal. A: Chem. 2005, 240, 55-60
23. Yamada, Y. M. A.; Uozumi, Y. Org. Lett. 2006, 8, 1375-1378
24. Chen, B. W. J.; Chng, L. L.; Yang, J.; Wei, Y.; Yang, J.; Ying, J. Y. ChemCatChem 2013, 5, 277-283
25. Xu, G.; Li, Q.; Feng, J.; Liu, Q.; Zhang, Z.; Wang, X.; Zhang, X.; Mu, X. ChemSusChem 2014, 7, 105-109
26. Fischer, A.; Makowski, P.; Muller, J. O.; Antonietti, M.; Thomas, A.; Goettmann, F. ChemSusChem 2008, 1, 444-449
27. Alonso, F.; Riente, P.; Yus, M. Eur. J. Org. Chem. 2008, 4908-4914
28. Liao, S.; Yu, K.; Li, Q.; Tian, H.; Zhang, Z.; Yu, X.; Qing, X. Org. Biomol. Chem. 2012, 10, 2973-2978
29. Buil, M. L.; Esteruelas, M. A.; Herrero, J.; Izquierdo, S.; Pastor, I. M.; Yus, M. ACS Catal. 2013, 3, 2072-2075
30. Kuwahara, T.; Fukuyama, T.; Ryu, I. Org. Lett. 2012, 14, 4703-4705
31. Qu, P.; Sun, C.; Ma, J.; Li, F. Adv. Synth. Catal. 2014, 356, 447-459
32. Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Kasuga, K. J. Am. Chem. Soc. 2005, 127, 13118-13119
33. Wang, W.; Muckerman, J. T.; Fujita, E.; Himeda, Y. ACS Catal. 2013, 3, 856-860
34. Kawahara, R.; Fujita, K.; Yamaguchi, R. J. Am. Chem. Soc. 2012, 134, 3643-3646
35. DePasquale, J.; Nieto, I.; Reuther, L. E.; Herbst-Gervasoni, C. J.; Paul, J. J.; Mochalin, V.; Zeller, M.; Thomas, C. M.; Addison, A. W.; Papish, E. T. Inorg. Chem. 2013, 52, 9175-9183
36. Kawahara, R.; Fujita, K.; Yamaguchi, R. Angew. Chem., Int. Ed. 2012, 51, 12790-12794
37. Fujita, K.; Tanaka, Y.; Kobayashi, M.; Yamaguchi, R. J. Am. Chem. Soc. 2014, 136, 4829-4832
38. Li, F.; Shan, H.; Chen, L.; Kang, Q.; Zou, P. Chem. Commun. 2012, 48, 603-605
39. Li, F.; Kang, Q.; Shan, H.; Chen, L.; Xie, J. Eur. J. Org. Chem. 2012, 5085-5092
40. Li, F.; Xie, J.; Shan, H.; Sun, C.; Chen, L. RSC Adv. 2012, 2, 8645-8652
41. Li, F.; Chen, L.; Kang, Q.; Cai, J.; Zhu, G. New J. Chem. 2013, 37, 624-631
42. Li, F.; Sun, C.; Shan, H.; Zou, X.; Xie, J. ChemCatChem 2013, 5, 1543-1552
43. Li, F.; Qu, P.; Ma, J.; Zou, X.; Sun, C. ChemCatChem 2013, 5, 2178-2182
44. Sun, C.; Zou, X.; Li, F. Chem.-Eur. J. 2013, 19, 14030-14033
45. Ma, J.; Wang, N.; Li, F. Asian J. Org. Chem. 2014, 3, 940-947
46. Wang, N.; Zou, X.; Ma, J.; Li, F. Chem. Commun. 2014, 50, 8303-8305
47. Li, F.; Sun, C.; Wang, N. J. Org. Chem. 2014, 79, 8031-8039
48. Fujita, K.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2002, 4, 2691-2694
49. Fujita, K.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525-3528
50. Fujita, K.; Asai, C.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi, R. Org. Lett. 2005, 7, 4017-4019
51. Lofberg, C.; Grigg, R.; Whittaker, M. A.; Keep, A.; Derrick, A. J. Org. Chem. 2006, 71, 8023-8027
52. Prades, A.; Corberan, R.; Poyatos, M.; Peris, E. Chem.-Eur. J. 2008, 14, 11474-11479
53. Gnanamgari, D.; Sauer, E. L. O.; Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H. Organometallics 2009, 28, 321-325
54. Blank, B.; Michlik, S.; Kempe, R. Chem.-Eur. J. 2009, 15, 3790-3799
55. Blank, B.; Kempe, R. J. Am. Chem. Soc. 2010, 132, 924-925
56. Iuchi, Y.; Obora, Y.; Ishii, Y. J. Am. Chem. Soc. 2010, 132, 2536-2537
57. Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193-13198
58. Andrushko, N.; Andrushko, V.; Roose, P.; Moonen, K.; Boner, A. ChemCatChem 2010, 2, 640-643
59. Anxionnat, B.; Pardo, D. G.; Ricci, G.; Cossy, J. Org. Lett. 2011, 13, 4084-4087
60. Kawahara, R.; Fujita, K.; Yamaguchi, R. Adv. Synth. Catal. 2011, 353, 1161-1168
61. Berliner, M. A.; Dubant, S. P. A.; Makowski, T.; Ng, K.; Sitter, B.; Wager, C.; Zhang, Y. Org. Process Res. Dev. 2011, 15, 1052-1062
62. Wetzel, A.; Wockel, S.; Schelwies, M.; Brinks, M. K.; Rominger, F.; Hofmann, P.; Limbach, M. Org. Lett. 2013, 15, 266-269
63. Guo, L.; Liu, Y.; Yao, W.; Leng, X.; Huang, Z. Org. Lett. 2013, 15, 1144-1147
64. Qian, M.; Liauw, M. A.; Emig, G. Appl. Catal., A 2003, 238, 211-222
65. Lin, W. H.; Chang, H. F. Catal. Today 2004, 97, 181-188
66. Tani, K.; Iseki, A.; Yamagata, T. Chem. Commun. 1999, 1821-1822
67. Moran, J.; Preetz, A.; Mesch, R. A.; Krische, M. J. Nat. Chem. 2011, 3, 287-290
68. Chan, L. K. M.; Poole, D. L.; Shen, D.; Healy, M. P.; Donohoe, T. J. Angew. Chem., Int. Ed. 2014, 53, 761-765
69. Ogawa, S.; Obora, Y. Chem. Commun. 2014, 50, 2491-2493
70. Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 285-287
71. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739
72. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
73. Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186-2187
74. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300-1308
75. Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090-1100
76. Johnson, J. B.; Backvall, Jan-E. J. Org. Chem. 2003, 68, 7681-7684
77. Conley, B. L.; Pennington-Boggio, M. K.; Boz, E.; Williams, T. J. Chem. Rev. 2010, 110, 2294-2312
78. III complexes; see Campos, J.; Hintermair, U.; Brewster, T. P.; Takase, M. K.; Crabtree, R. H. ACS Catal. 2014, 4, 973-985
79. Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903-4910
80. Ziessel, R. J. Chem. Soc., Chem. Commun. 1988, 16-17
81. Scheeren, C.; Maasarani, F.; Hijazi, A.; Djukic, J. P.; Pfeffer, M.; Zaric, S. D.; Goff, X. F. L.; Ricard, L. Organometallics 2007, 26, 3336-3345
82. Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470-5474
83. Kawahara, R.; Fujita, K.; Yamaguchia, R. Adv. Synth. Catal. 2011, 353, 1161-1168
84. Ball, R. G.; Graham, W. A. G.; Heinekey, D. M.; Hoyano, J. K.; McMaster, A. D.; Mattson, B. M.; Michel, S. T. Inorg. Chem. 1990, 29, 2023-2025
85. Yang, D.; Long, Y.; Wang, H.; Zhang, Z. Org. Lett. 2008, 10, 4723-4726
86. Stroba, A.; Schaeffer, F.; Hindie, V.; Lopez-Garcia, L.; Adrian, I.; Frohner, W.; Hartmann, R. W.; Biondi, R. M.; Engel, M. J. Med. Chem. 2009, 52, 4683-4693
87. Feng, Y.; Yang, C.; Huang, Q.; Xu, H. Tetrahedron 2012, 68, 5053-5059
88. Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2005, 61, 2217-2231
89. Weickmann, D.; Plietker, B. ChemCatChem 2013, 5, 2170-2173
90. Yang, D.; Zhou, Y.; Xue, N.; Qu, J. J. Org. Chem. 2013, 78, 4171-4176
91. Wu, X.; Tiekink, E. R. T.; Kostetski, I.; Kocherginsky, N.; Tan, A. L. C.; Khoo, S. B.; Wilairat, P.; Go, M. L. Eur. J. Pharm. Sci. 2006, 27, 175-187
92. Cabrero-Antonino, J. R.; Leyva-Perez, A.; Corma, A. Chem.-Eur. J. 2012, 18, 11107-11114
93. Rahain, R. J.; Maleczka, R. E. Org. Lett. 2011, 13, 584-587
94. Ruan, J.; Saidi, J.; Iggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510-10511
95. Vellakkaran, M.; Andappan, M. M. S.; Kommu, N. Eur. J. Org. Chem. 2012, 4694-4698
96. Colbon, P.; Ruan, J.; Purdie, M.; Xiao, J. Org. Lett. 2010, 12, 3670-3673
97. Jean, M.; Renault, J.; Uriac, P.; Capet, M.; Weghe, P. Org. Lett. 2007, 9, 3623-3625
98. Lindale, M. G.; Liebeskind, L. S. J. Am. Chem. Soc. 2011, 133, 6403-6410
99. Jiang, Q.; Guo, T.; Wang, Q.; Wu, P.; Yu, Z. Adv. Synth. Catal. 2013, 355, 1874-1880
100. Lu, W. J.; Chen, Y. W.; Hou, X. L. Adv. Synth. Catal. 2010, 352, 103-107
101. Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316-1327
102. Fernandez, R.; Ferrete, A.; Llera, J. M.; Magriz, A.; Martin-Zamora, E.; Diez, E.; Lassaletta, J. M. Chem.-Eur. J. 2004, 10, 737-745
103. Womack, G. B.; Angeles, J. G.; Fanelli, V. E.; Indradas, B.; Snowden, R. L.; Sonnay, P. J. Org. Chem. 2009, 74, 5738-5741