Palladium- and nickel-catalyzed aminations of aryl imidazolylsulfonates and sulfamates

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1784-1786

  Ackermann, Lutz ^a   Sandmann, René ^a   Song, Weifeng ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953191516     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200267b     Document Type: Article

References (51)

1. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27-50
2. Klinkenberg, J. L.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 86-95
3. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971
4. Krüger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153-2167
5. Ackermann, L. Synlett 2007, 507-526
6. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599-1626
7. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, DOI: 10.1021/cr100259t.
8. Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 1728-1759
9. Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486-1495
10. Littke, A. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009; pp 25 - 67.
11. Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002; pp 330 - 367.
12. Select reviews: Högermeier, J.; Reissig, H.-U. Adv. Synth. Catal. 2009, 351, 2747-2763
13. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680
14. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85-126
15. For representative examples of catalyzed arylations with tosylates or mesylates, see: C-N bond formation: Mantel, M. L. H.; Lindhardt, A. T.; Lupp, D.; Skrydstrup, T. Chem.-Eur. J. 2010, 16, 5437-5442
16. Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 8686-8690
17. So, C. M.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 6402-6406
18. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819
19. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704-8705
20. Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655
21. Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911-913
22. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370 and references cited herein See also: Ackermann, L.; Fenner, S. Chem. Commun. 2011, 47, 430-432
23. Yeung, P. Y.; So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2010, 49, 8918-8922
24. Wilson, D. A.; Wilson, C. J.; Moldoveanu, C.; Resmerita, A.-M.; Corcoran, P.; Hoang, L. M.; Rosen, B. M.; Percec, V. J. Am. Chem. Soc. 2010, 132, 1800-1801
25. Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2010, 75, 5109-5112
26. Bhayana, B.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2009, 11, 3954-3957
27. Ackermann, L.; Althammer, A.; Fenner, S. Angew. Chem., Int. Ed. 2009, 48, 201-204
28. So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 8059-8063
29. Zhang, L.; Wu, J. Adv. Synth. Catal. 2008, 350, 2409-2413
30. Zhang, L.; Wu, J. J. Am. Chem. Soc. 2008, 130, 12250-12251
31. Hansen, A. L.; Ebran, J.-P.; Ahlquist, M.; Norrby, P.-O.; Skrydstrup, T. Angew. Chem., Int. Ed. 2006, 45, 3349-3353
32. Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457-3460
33. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530 and references cited therein
34. Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519-2522
35. When, P. M.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688
36. Albaneze-Walker, J.; Raju, R.; Vance, J. A.; Goodman, A. J.; Reeder, M. R.; Liao, J.; Maust, M. T.; Irish, P. A.; Espino, P.; Andrews, D. R. Org. Lett. 2009, 11, 1463-1466
37. Goegsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2009, 11, 4886-4888
38. Ackermann, L.; Barfüsser, S.; Pospech, J. Org. Lett. 2010, 12, 724-726
39. Luo, Y.; Wu, J. Organometallics 2009, 28, 6823-6826
40. Shirbin, S. J.; Boughton, B. A.; Zammit, S. C.; Zanatta, S. D.; Marcuccio, S. M.; Hutton, C. A.; Williams, S. J. Tetrahedron Lett. 2010, 51, 2971-2974
41. Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748-17749 and references cited therein
42. For nickel-catalyzed aminations of aryl pivalates, see: Shimasaki, T.; Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2010, 49, 2929-2932
43. After submission of our manuscript, a nickel -catalyzed amination of aryl sulfamates was reported by Garg and coworkers: Ramgren, S. D.; Silberstein, A. L.; Yang, Y.; Garg, N. K. Angew. Chem., Int. Ed. 2011, 50, DOI: 10.1002/anie.201007325.
44. For representative examples, see: Ackermann, L.; Song, W.; Sandmann, R. J. Organomet. Chem. 2011, 696, 195-201
45. Ackermann, L.; Barfüsser, S.; Potukuchi, H. K. Adv. Synth. Catal. 2009, 351, 1064-1072
46. Ackermann, L.; Sandmann, R.; Kaspar, L. T. Org. Lett. 2009, 11, 2031-2034
47. Ackermann, L.; Sandmann, R.; Kondrashov, M. V. Synlett 2009, 1219-1222
48. Ackermann, L.; Sandmann, R.; Villar, A.; Kaspar, L. T. Tetrahedron 2008, 64, 769-777
49. Ackermann, L.; Spatz, J. H.; Gschrei, C. J.; Born, R.; Althammer, A. Angew. Chem., Int. Ed. 2006, 45, 7627-7630
50. Ackermann, L.; Born, R. Angew. Chem., Int. Ed. 2005, 44, 2444-2447 and references cited therein
51. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361