Recent advances in iridium-catalyzed alkylation of C-H and N-H bonds

ACS Catalysis

Volumn 3, Issue 4, 2013, Pages 704-712

  Pan, Shiguang ^a   Shibata, Takanori ^a,b  

^a WASEDA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

alcohols; alkenes; alkylation; carbonates; iridium

Indexed keywords

ALLYL CARBONATES; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; IRIDIUM CATALYST; IRIDIUM COMPLEX;

ALCOHOLS; ALKYLATION; CARBONATES; HYDROCARBONS; IRIDIUM; OLEFINS;

IRIDIUM COMPOUNDS;

EID: 84875916293     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs400066q     Document Type: Review

References (76)

1. Dyker, G., Eds.; Handbook of C-H Transformations; Wiley-VCH: Weinchem, Germany, 2005.
2. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710
3. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971
4. Yu, J.-Q.; Shi, Z., Eds.; C-H Activation; Springer-Verlag: Berlin, Germany, 2010.
5. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
6. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083
7. Oro, L. A.; Claver, C., Eds.; Iridium Complexes in Organic Synthesis; Wiely-VCH: Verlag GMBH: Weinheim, 2009.
8. Gill, D. S.; Maitlis, P. M. J. Organomet. Chem. 1975, 87, 359-364
9. Fujita, K.; Yamaguchi, R. Synlett 2005, 560-571
10. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681-703
11. Guillena, G.; Ramón, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611-1641
12. Suzuki, T. Chem. Rev. 2011, 111, 1825-1845
13. Obora, Y.; Ishii, Y. Synlett 2011, 30-51
14. Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675-691
15. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72-73
16. Onodera, G.; Nishibayashi, Y.; Uemura, S. Angew. Chem., Int. Ed. 2006, 45, 3819-3822
17. Xu, C.; Dong, X.-M.; Wang, Z.-P.; Hao, X.-Q.; Li, Z.; Duan, L.-M.; Ji, B.-M.; Song, M.-Q. J. Organomet. Chem. 2012, 700, 214-218
18. Rueping, M.; Phapale, V. B. Green Chem. 2012, 14, 55-57
19. Baht, S.; Sridharan, V. Chem. Commun. 2012, 48, 4701-4703
20. Iuchi, Y.; Obora, Y.; Ishii, Y. J. Am. Chem. Soc. 2010, 132, 2536-2537
21. Black, P. J.; Cami-Kobeci, G.; Edwards, M. G.; Slatford, P. A.; Whittlesey, M. K.; Williams, J. M. J. Org. Biomol. Chem. 2006, 4, 116-125
22. Löfberg, C.; Grigg, R.; Keep, A.; Derrick, A.; Sridharan, V.; Kilner, C. Chem. Commun. 2006, 5000-5002
23. Morita, M.; Obora, Y.; Ishii, Y. Chem. Commun. 2007, 2850-2852
24. Grigg, R.; Löfberg, C.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 849-854
25. Iuchi, Y.; Hyotanishi, M.; Miller, B. E.; Maeda, K.; Obora, Y.; Ishii, Y. J. Org. Chem. 2010, 75, 1803-1806
26. Löfberg, C.; Grigg, R.; Whittaker, M. A.; Keep, A.; Derrick, A. J. Org. Chem. 2006, 71, 8023-8027
27. Maeda, K.; Obora, Y.; Sakaguchi, S.; Ishii, Y. Bull. Chem. Soc. Jpn. 2008, 81, 689-696
28. Anxionnat, B.; Pardo, D. G.; Ricci, G.; Cossy, J. Org. Lett. 2011, 13, 4084-4087
29. Sawaguchi, T.; Obora, Y. Chem. Lett. 2011, 40, 1055-1057
30. Anxionnat, B.; Pardo, D. G.; Ricci, G.; Cossy, J. Eur. J. Org. Chem. 2012, 4453-4456
31. Whitney, S.; Grigg, R.; Derrick, A.; Keep, A. Org. Lett. 2007, 9, 3299-3302
32. Wong, C. M.; Vuong, K. Q.; Gatus, M. R. D.; Hua, C.; Bhadbhade, M.; Messerle, B. A. Organometallics 2012, 31, 7500-7510
33. Blank, B.; Kempe, R. J. Am. Chem. Soc. 2010, 132, 924-925
34. Obora, Y.; Ogawa, S.; Yamamoto, N. J. Org. Chem. 2012, 77, 9429-9433
35. Fujita, K.; Yamaguchi, R. Iridium Complexes in Organic Synthesis; Oro, L. A.; Claver, C., Eds.; Wiley-VCH Verlag GMBH: Weinheim, 2009; pp 107-143.
36. Gnanamgari, D.; Sauer, E. L. O.; Scheley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H. Organometallics 2009, 28, 321-325
37. Zhu, M.; Fujita, K.; Yamaguchi, R. Org. Lett. 2010, 12, 1336-1339
38. Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.; Williams, J. M. J. Chem. Commun. 2010, 46, 1541-1543
39. Zhang, W.; Dong, X.; Zhao, W. Org. Lett. 2011, 13, 5386-5389
40. Li, F.; Shan, H.; Chen, L.; Kang, Q.; Zou, P. Chem. Commun. 2012, 48, 603-605
41. Li, F.; Kang, Q.; Shan, H.; Chen, L.; Xie, J. Eur. J. Org. Chem. 2012, 5085-5092
42. Blank, B.; Michlik, S.; Kempe, R. Chem.-Eur. J. 2009, 15, 3790-3799
43. Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193-13198
44. Michlik, S.; Hille, T.; Kempe, R. Adv. Synth. Catal. 2012, 354, 847-862
45. Michlik, S.; Kempe, R. Nat. Chem. 2013, 5, 140-144
46. Kawahara, R.; Fujita, K.; Yamaguchi, R. J. Am. Chem. Soc. 2010, 132, 15108-15111
47. Ohta, H.; Yuyama, Y.; Uozumi, Y.; Yamada, Y. M. A. Org. Lett. 2011, 13, 3892-3895
48. Kuo, H.-Y.; Liu, Y.-H.; Peng, S.-M.; Liu, S.-T. Organometallics 2012, 31, 7248-7255
49. Bartoszewicz, A.; Marcos, R.; Sahoo, S.; Inge, A. K.; Zou, X.; Martín-Matute, B. Chem.-Eur. J. 2012, 18, 14510-14519
50. Trost, B. M.; Lee, C. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiely-VCH Verlag GMBH: New York, 2000; pp 593-649.
51. Takeuchi, R.; Kezuka, S. Synthesis 2006, 3349-3366
52. Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Org. Lett. 2008, 10, 1815-1818
53. Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Synthesis 2009, 2076-2082
54. Xu, Q.-L.; Dai, L.-X.; You, S.-L. Chem. Sci. 2013, 4, 97-102
55. Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 2579-2581
56. Stanley, L. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2009, 48, 7841-7844
57. Liu, W.-B.; Zhang, X.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 5183-5187
58. Daugulis, O. Top. Curr. Chem. 2010, 292, 57-84
59. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
60. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
61. Dorta, R.; Togni, A. Chem. Commun. 2003, 760-761
62. Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.-K.; Endo, K.; Shibata, T. J. Organomet. Chem. 2008, 693, 3939-3942
63. Takebayashi, S.; Shibata, T. Organometallics 2012, 31, 4114-4117
64. Pan, S.; Ryu, N.; Shibata, T. J. Am. Chem. Soc. 2012, 134, 17474-17477
65. Sevov, C. S.; Hartwig, J. F. J. Am. Soc. Chem. 2013, 135, 2116-2119
66. Tsuchikama, K.; Kasagawa, M.; Endo, K.; Shibata, T. Org. Lett. 2009, 11, 1821-1823
67. Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2011, 13, 4692-4695
68. Pan, S.; Matsuo, Y.; Endo, K.; Shibata, T. Tetrahedron 2012, 68, 9009-9015
69. Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795-3892
70. Hesp, K. D.; Stradiotto, M. ChemCatChem 2010, 2, 1192-1207
71. Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819-1824
72. Nugent, T., Ed.; Chiral Amine Synthesis: Methods, Developments and Applications; Wiley-VCH: Weinheim, Germany, 2010.
73. Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857-10858
74. Zhou, J.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 12220-12221
75. Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2012, 14, 780-783
76. Sevov, C. S.; Zhou, J.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 11960-11963