Iridium-catalyzed selective α-alkylation of unactivated amides with primary alcohols

Organic Letters

Volumn 15, Issue 5, 2013, Pages 1144-1147

  Guo, Le ^a   Liu, Yinghua ^a   Yao, Wubing ^a   Leng, Xuebing ^a   Huang, Zheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874634918     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400360g     Document Type: Article

References (37)

1. Challis, B. C.; Challis, J. In The Chemistry of Amides; Zabicky, J., Ed.; John Wiley & Sons: London, 1970; pp 731-857.
2. Kim, H.; Lee, H.; Lee, D.; Kim, S.; Kim, D. J. Am. Chem. Soc. 2007, 129, 2269
3. O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070
4. Seebach, D.; Beck, A. K.; Bossler, H. G.; Gerber, C.; Ko, S. Y.; Murtiashaw, C. W.; Naef, R.; Shoda, S.-I.; Thaler, A.; Krieger, M.; Wenger, R. Helv. Chim. Acta 1993, 76, 1564
5. Bähn, S.; Imm, S.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 1853
6. Suzuki, T. Chem. Rev. 2011, 111, 1825
7. Obora, Y.; Ishii, Y. Synlett 2011, 30
8. Saidi, O.; Williams, J. M. J. Iridium Catalysis 2011, 34, 77
9. Watson, A. J. A.; Williams, J. M. J. Science 2010, 329, 635
10. Guillena, G.; J. Ramón, D.; Yus, M. Chem. Rev. 2009, 110, 1611
11. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2009, 110, 681
12. Fujita, K.; Yamaguchi, R. Synlett 2005, 560
13. Blank, B.; Kempe, R. J. Am. Chem. Soc. 2010, 132, 924
14. Obora, Y.; Ogawa, S.; Yamamoto, N. J. Org. Chem. 2012, 77, 9429
15. Grigg, R.; Löfberg, C.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 849
16. Pridmore, S. J.; Williams, J. M. J. Tetrahedron Lett. 2008, 49, 7413
17. Morita, M.; Obora, Y.; Ishii, Y. Chem. Commun. 2007, 2850
18. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 126, 72
19. Iuchi, Y.; Obora, Y.; Ishii, Y. J. Am. Chem. Soc. 2010, 132, 2536
20. Foo, S. W.; Oishi, S.; Saito, S. Tetrahedron Lett. 2012, 53, 5445
21. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
22. Fersner, A.; Karty, J. M.; Mo, Y. J. Org. Chem. 2009, 74, 7245
23. Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 7346
24. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2001, 124, 392
25. Jensen, T.; Madsen, R. J. Org. Chem. 2009, 74, 3990
26. Grigg, R.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 4375
27. Grigg, R.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 7468
28. Morales-Morales, D.; Redón, R.; Wang, Z.; Lee, D. W.; Yung, C.; Magnuson, K.; Jensen, C. M. Can. J. Chem. 2001, 79, 823
29. Gu, X.-Q.; Chen, W.; Morales-Morales, D.; Jensen, C. M. J. Mol. Catal. A: Chem. 2002, 189, 119
30. Bernskoetter, W. H.; Brookhart, M. Organometallics 2008, 27, 2036
31. Choi, J.; MacArthur, A. H. R.; Brookhart, M.; Goldman, A. S. Chem. Rev. 2011, 111, 1761
32. The Chemistry of Pincer Compounds; Morales-Morales, D.; Jensen, C., Eds.; Elsevier: Amsterdam, 2007.
33. Binyamin, I.; Pailloux, S.; Duesler, E. N.; Paine, R. T.; Hay, B. P.; Rapko, B. M. J. Heterocycl. Chem. 2007, 44, 99
34. Ben-Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390
35. He, L.-P.; Chen, T.; Xue, D.-X.; Eddaoudi, M.; Huang, K.-W. J. Organomet. Chem. 2012, 700, 202
36. Michlik, S.; Hille, T.; Kempe, R. Adv. Synth. Catal. 2012, 354, 847
37. Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193