Iridium-catalyzed, intermolecular hydroamination of unactivated alkenes with indoles

Journal of the American Chemical Society

Volumn 136, Issue 8, 2014, Pages 3200-3207

  Sevov, Christo S ^a,b   Zhou, Jianrong ^b   Hartwig, John F ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED ALKENES; ALKYL AMINES; CATALYST RESTING STATE; COMPUTATIONAL DATA; HYDROAMINATIONS; INSERTION REACTIONS; KINETIC DATA; UNACTIVATED OLEFINS;

IRIDIUM; OLEFINS; REACTION KINETICS;

ADDITION REACTIONS;

ALKENE DERIVATIVE; DEUTERIUM; HYDROGEN; INDOLE DERIVATIVE; IRIDIUM; LIGAND; NITROGEN;

ADDITION REACTION; ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; CYCLIZATION; HYDROAMINATION; HYDROGEN BOND; HYDROGENATION; ISOTOPE LABELING; KINETICS; SYNTHESIS;

EID: 84896888823     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja412116d     Document Type: Article

References (56)

1. Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685
2. Kim, J.; Movassaghi, M. Chem. Soc. Rev. 2009, 38, 3035
3. Joule, J. A.; Mills, K. Heterocyclic Chemistry; John Wiley & Sons: New York, 2010.
4. Sundberg, R. J.; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. S. Indoles; Elsevier Science: Waltham, MA, 1996.
5. Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550
6. Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199
7. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
8. Stanley, L. M.; Hartwig, J. F. Angew. Chem. 2009, 121, 7981
9. Cui, H.-L.; Feng, X.; Peng, J.; Lei, J.; Jiang, K.; Chen, Y.-C. Angew. Chem., Int. Ed. 2009, 48, 5737
10. Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis: Reduction; Elsevier Science & Technology Books: Waltham, MA, 1991.
11. Robinson, B. Chem. Rev. 1969, 69, 785
12. Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1973, 499
13. Hartwig, J. F. In Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010; Vol. 1, p 700.
14. Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795
15. Hesp, K. D.; Stradiotto, M. ChemCatChem 2010, 2, 1192
16. Hannedouche, J.; Schulz, E. Chem.-Eur. J. 2013, 19, 4972
17. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673
18. Dunne, J. F.; Fulton, D. B.; Ellern, A.; Sadow, A. D. J. Am. Chem. Soc. 2010, 132, 17680
19. Hesp, K. D.; Tobisch, S.; Stradiotto, M. J. Am. Chem. Soc. 2010, 132, 413
20. Julian, L. D.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 13813
21. Shen, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2010, 49, 564
22. Leitch, D. C.; Platel, R. H.; Schafer, L. L. J. Am. Chem. Soc. 2011, 133, 15453
23. Liu, Z.; Yamamichi, H.; Madrahimov, S. T.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2772
24. Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584
25. Brunet, J. J.; Chu, N. C.; Diallo, O. Organometallics 2005, 24, 3104
26. Karshtedt, D.; Bell, A. T.; Tilley, T. D. J. Am. Chem. Soc. 2005, 127, 12640
27. Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798
28. For a seminal example of asymmetric, intermolecular hydroamination of unactivated alkenes with gold, see: Zhang, Z.; Lee, S. D.; Widenhoefer, R. A. J. Am. Chem. Soc. 2009, 131, 5372
29. For a seminal example of asymmetric, intermolecular hydroamination of unactivated alkenes with lanthanides, see: Reznichenko, A. L.; Nguyen, H. N.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2010, 49, 8984
30. Sevov, C. S.; Zhou, J.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 11960
31. Brunet, J.-J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221
32. Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857
33. McBee, J. L.; Bell, A. T.; Tilley, T. D. J. Am. Chem. Soc. 2008, 130, 16562
34. Zhou, J.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 12220
35. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546
36. Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286
37. Qian, H.; Widenhoefer, R. A. Org. Lett. 2005, 7, 2635
38. Pan, S. G.; Endo, K.; Shibata, T. Org. Lett. 2012, 14, 780
39. Nishina, N.; Yamamoto, Y. Synlett 2007, 1767
40. Butler, K. L.; Tragni, M.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2012, 51, 5175
41. Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366
42. Johns, A. M.; Sakai, N.; Ridder, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9306
43. Brunet, J.-J.; Cadena, M.; Chu, N. C.; Diallo, O.; Jacob, K.; Mothes, E. Organometallics 2004, 23, 1264
44. Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649
45. Cao, P.; Cabrera, J.; Padilla, R.; Serra, D.; Rominger, F.; Limbach, M. Organometallics 2012, 31, 921
46. Sevov, C. S.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2116
47. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738
48. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328
49. Hanley, P. S.; Marković, D.; Hartwig, J. F. J. Am. Chem. Soc., 2010, 132, 6302
50. Neukom, J. D.; Perch, N. S.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 6276
51. Hanley, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 15661
52. Weinstein, A. B.; Stahl, S. S. Angew. Chem., Int. Ed. 2012, 51, 11505
53. Hanley, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2013, 52, 8510
54. Tye, J. W.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 14703
55. Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115
56. Hartwig, J. F. In Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010; Vol. 1, p 349.