Radical transfer hydroamination with aminated cyclohexadienes using polarity reversal catalysis: Scope and limitations

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4498-4503

  Guin, Joyram ^a   Mück Lichtenfeld, Christian ^a   Grimme, Stefan ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC PROTONS; ARYLBROMIDES; MARKOVNIKOV SELECTIVITY; PHOSPHONATES;

ALCOHOLS; AROMATIC COMPOUNDS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; ELECTRONS; ETHERS; FREE RADICALS;

SYNTHESIS (CHEMICAL);

ALCOHOL DERIVATIVE; AMIDE; BROMINE DERIVATIVE; CYCLOALKENE; IMIDE; PHOSPHONIC ACID DERIVATIVE; PROTON; SILANE DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; SYNTHESIS;

EID: 34247130947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0692581     Document Type: Article

References (69)

1. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
2. Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579.
3. For a review of hydroaminations of alkynes, see: Doye, S. Synlett 2004, 1653.
4. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. Hart, D. J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 279.
6. Lee, E. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 303.
7. Reviews: Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337.
8. Zard, S. Z. Synlett 1996, 1148.
9. Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
10. Stella L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 407.
11. Amidyl radicals from N-chloroamides: Mackiewicz, P.; Furstoss, R.; Waegell, B.; Cote, R.; Lessard, J. J. Org. Chem. 1978, 43, 3746.
12. Lessard, J.; Cote, R.; Mackiewicz, P.; Furstoss, R.; Waegell, B. J. Org. Chem. 1978, 43, 3750.
13. Göttlich, R. Synthesis 2000, 1561.
14. Heuger, G.; Kalsow, S.; Göttlich, R. Eur. J. Org. Chem. 2002, 1848.
15. Schulte-Wülwer, I. A.; Helaja, J.; Göttlich, R. Synthesis 2003, 1886.
16. Amidyl radicals from sulfenamides: Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1993, 34, 6877.
17. Amidyl radicals from PTOC-derivatives: Newcomb, M.; Esker, J. L. Tetrahedron Lett. 1991, 32, 1035.
18. Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1992, 33, 5913.
19. Esker, J. L.; Newcomb, M. J. Org. Chem. 1993, 58, 4933.
20. Esker, J. L.; Newcomb, M. J. Org. Chem. 1994, 59, 2779.
21. For other amidyl radical precursors, see: Hoang-Cong, X.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1999, 40, 2125.
22. Lin, X.; Stien, D.; Weinreb, S. M. Tetrahedron Lett. 2000, 41, 2333.
23. Gagosz, F.; Moutrille, C.; Zard, S. Z. Org. Lett. 2002, 4, 2707.
24. Moutrille, C.; Zard, S. Z. Chem. Commun. 2004, 1848.
25. Recent examples on intermolecular addition of N-centered radicals: Tsuritani, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 3246.
26. Kitagawa, O.; Miyaji, S.; Yamada, Y.; Fujiwara, H.; Taguchi, T. J. Org. Chem. 2003, 68, 3184.
27. Kitagawa, O.; Yamada, Y.; Fujiwara, H.; Taguchi, T. Angew. Chem., Int. Ed. 2001, 40, 3865.
28. Mackiewicz, P.; Furstoss, R. Tetrahedron 1978, 34, 3241.
29. Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y.-L.; Sugita, K.; Zou, N. Angew. Chem., Int. Ed. 2001, 40, 202.
30. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233.
31. Janza, B.; Studer, A. J. Org. Chem. 2005, 70, 6991.
32. Reviews: Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812.
33. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
34. Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794.
35. Kemper, J.; Studer, A. Angew. Chem., Int. Ed. 2005, 44, 4914.
36. Baguley, P. A.; Walton, J. C. Angew. Chem., Int. Ed. 1998, 37, 3072.
37. Studer, A.; Amrein, S. Synthesis 2002, 835.
38. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
39. Bella, A. F.; Jackson, L. V.; Walton, J. C. Org. Biomol. Chem. 2004, 2, 421.
40. Alnajjar, M. S.; Franz, J. A. J. Am. Chem. Soc. 1992, 114, 1052.
41. Review: Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649.
42. Osborn, C. L.; Van Auken, T. V.; Trecker, D. J. J. Am. Chem. Soc. 1968, 90, 5806.
43. Beckwith, A. L. J.; Wagner, R. D. J. Org. Chem. 1981, 46, 3638.
44. Bruno, J. W.; Marks, T. J.; Lewis, F. D. J. Am. Chem. Soc. 1982, 104, 5580.
45. Kagayama, T.; Fuke, T.; Sakaguchi, S.; Ishii, Y. Bull. Chem. Soc. Jpn. 2005, 78, 1673.
46. Horner, J. C.; Musa, O. M.; Bouvier, A.; Newcomb, M. J. Am. Chem. Soc. 1998, 120, 7738.
47. Ahlrichs, R. et al. TURBOMOLE, vers. 5.7; Universität Karlsruhe: 2005.
48. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
49. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
50. Kind, C.; Reiher, M.; Neugebauer, J.; Hess, B. A. SNF, version 2.2.1; Universität Erlangen: 2002.
51. Studer, A.; Amrein, S.; Schleth, F.; Schulte, T.; Walton, J. C. J. Am. Chem. Soc. 2003, 125, 5726.
52. Zipse, H. Top. Curr. Chem. 2006, 263, 163.
53. Recent publications on Markovnikov hydroaminations: Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
54. Han, X.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2006, 45, 1747.
55. Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, 1744.
56. Komeyama, K.; Morimoto, T.; Takaki, K. Angew. Chem., Int. Ed. 2006, 45, 2938.
57. Sun, J.; Kozmin, S. A. Angew. Chem., Int. Ed. 2006, 45, 4991.
58. Widenhoefer, R. A.; Han, X. Eur. J. Org. Chem. 2006, 4555.
59. Nishina, N.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3314.
60. Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 1611.
61. Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179.
62. Taylor, J. G.; Whittall, N.; Hii, K. K. Org. Lett. 2006, 8, 3561.
63. Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367.
64. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
65. Anti-Markovnikov hydroaminations: Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 6042.
66. Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702.
67. Zhang, Z.; Schafer, L. L. Org. Lett. 2003, 5, 4733.
68. Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080.
69. Binmore, G.; Walton, J. C.; Cardellini, L. J. Chem. Soc., Chem. Commun. 1995, 27.