Copper-catalyzed amination of primary benzylic C?H bonds with primary and secondary sulfonamides

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2726-2729

  Powell, David A ^a   Fan, Hope ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; FUNCTIONALIZATIONS; H-BONDS; ROOM TEMPERATURE;

AMINES; HYDROCARBONS; SULFUR COMPOUNDS;

AMIDES;

BENZYL DERIVATIVE; COPPER; SULFONAMIDE; TOLUENE;

AMINATION; ARTICLE; CATALYSIS; HYDROGEN BOND; REACTION ANALYSIS; SYNTHESIS;

AMINATION; BENZENE; CARBON; CATALYSIS; COPPER; HYDROGEN; SULFONAMIDES;

EID: 77950970848     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100197r     Document Type: Article

References (93)

1. For some recent reviews of C?H bond oxidations, including aminations, see: Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061-5074
2. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242-3272
3. Díaz-Requejo, M. M.; Prez, P. J. Chem. Rev. 2008, 108, 3379-3394
4. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439-2463
5. Du Bois, J. Chemtracts 2005, 18, 1-13
6. Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed; Wiley-VCH: Weinheim, 2005; pp 379 ? 416.
7. Halfen, J. A. Curr. Org. Chem. 2005, 9, 657-669
8. For some recent reviews of metal-nitrene based aminations, see: Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417-424
9. Mller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919
10. Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586
11. Representative intramolecular metal-nitrene based aminations: Fiori, K. W.; Espino, C. G.; Brodsky, B. H.; Du Bois, J. Tetrahedron 2009, 65, 3042-3051
12. Kurokawa, T.; Kim, M.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 2777-2779
13. Olson, D. E.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 11248-11249
14. Milczek, E.; Boudet, N.; Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825-6828
15. Lebel, H.; Leogane, O.; Huard, K.; Lectard, S. Pure Appl. Chem. 2006, 78, 363-375
16. Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073-1076
17. Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198-14199
18. Zhang, J.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2005, 46, 5403-5408
19. Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379
20. Cui, Y.; He, C. Angew. Chem., Int. Ed. 2004, 43, 4210-4212
21. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Che, C.-M. J. Org. Chem. 2004, 69, 3610-3619
22. Fruit, C.; Mller, P. Helv. Chim. Acta 2004, 87, 1607-1615
23. Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468
24. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936
25. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598-600
26. Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728-6729
27. Representative intermolecular metal-nitrene based aminations: Lu, H.; Subbarayan, V.; Tao, J.; Zhang, X. P. Organometallics 2010, 29, 389-393
28. Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961-9964
29. Huard, K.; Lebel, H. Chem. - Eur. J. 2008, 14, 6222-6230
30. Kalita, B.; Lamar, A. A.; Nicholas, K. M. Chem. Commun. 2008, 4291-4293
31. Liang, C.; Collet, F.; Robert-Peillard, F.; Mller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343-350
32. Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. Angew. Chem., Int. Ed. 2007, 46, 5184-5186
33. Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zhang, X. P. Chem. Commun. 2007, 4644-4646
34. Bhuyan, R.; Nicholas, K. M. Org. Lett. 2007, 9, 3957-3959
35. Lebel, H.; Huard, K. Org. Lett. 2007, 9, 639-642
36. Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562-568
37. Fructos, M. R.; Trofimenko, S.; Díaz-Requejo, M. M.; Prez, P. J. J. Am. Chem. Soc. 2006, 128, 11784-11791
38. Reddy, R. P.; Davies, H. M. L. Org. Lett. 2006, 8, 5013-5016
39. Liang, C.; Robert-Peillard, F.; Fruit, C.; Mller, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2006, 45, 4641-4644
40. Leung, S. K.-Y.; Tsui, W.-M.; Huang, J.-S.; Che, C.-M.; Liang, J.-L.; Zhu, N. J. Am. Chem. Soc. 2005, 127, 16629-16640
41. Yamawaki, M.; Tsutsui, H.; Kitagaki, S.; Anada, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 9561-9564
42. Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3339-3342
43. Chanda, B. M.; Vyas, R.; Bedekar, A. V. J. Org. Chem. 2001, 66, 30-34
44. Albone, D. P.; Aujla, P. S.; Taylor, P. C. J. Org. Chem. 1998, 63, 9569-9571
45. Metal-peroxycarbamate and perester based C?H aminations: Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2007, 9, 3813-3816
46. Pelletier, G.; Powell, D. A. Org. Lett. 2006, 8, 6031-6034
47. Smith, K.; Hupp, C. D.; Allen, K. L.; Slough, G. A. Organometallics 2005, 24, 1747-1755
48. Clark, J. S.; Roche, C. Chem. Commun. 2005, 5175-5177
49. Kohmura, Y.; Kawasaki, K.-i.; Katsuki, T. Synlett 1997, 1456-1458
50. Metal- N -halosuccinimide based C?H aminations: Liu, X.; Zhang, Y.; Wang, L.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 6207-6212
51. Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2008, 10, 1863-1866
52. Palladium-catalyzed allylic C?H aminations: Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707-11711
53. Reed, S. A.; Mazzotti, A. R.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11701-11706
54. Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733-4736
55. Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274-7276
56. Other representative saturated C?H bond amination strategies: Allen, C. P.; Benkovics, T.; Turek, A. K.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 12560-12561
57. Fan, R.; Li, W.; Pu, D.; Zhang, L. Org. Lett. 2009, 11, 1425-1428
58. Zalatan, D. N.; Du Bois, J. Synlett 2009, 143-146
59. Zhao, B.; Du, H.; Shi, Y. J. Am. Chem. Soc. 2008, 130, 7220-7221
60. Chouthaiwale, P. V.; Suryavanshi, G.; Sudalai, A. Tetrahedron Lett. 2008, 49, 6401-6403
61. Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. - Eur. J. 2003, 9, 249-259
62. Some of the increased challenge associated with oxidations of primary over secondary benzylic C?H bonds may be attributable to differences in bond-dissociation energies between these types of substrates, see refs 4b, 4n, and Bryant, J. R.; Mayer, J. M. J. Am. Chem. Soc. 2003, 125, 10351-10361
63. The amination of toluene with a variety of transition metal catalysts are reported to proceed in 9?30% yields even when toluene is used in large excess as the solvent. See Supporting Information for further details.
64. Kang, S.; Lee, H.-K. J. Org. Chem. 2010, 75, 237-240
65. Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631
66. Wang, S.; Romo, D. Angew. Chem., Int. Ed. 2008, 47, 1284-1286
67. Liu, Y.; Xiao, W.; Wong, M.-K.; Che, C.-M. Org. Lett. 2007, 9, 4107-4110
68. Fleming, J. J.; Du Bois, J. J. Am. Chem. Soc. 2006, 128, 3926-3927
69. Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511
70. Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951
71. Trost, B. M.; Gunzner, J. L.; Dirat, O.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 10396-10415
72. Overman, L. E.; Tomasi, A. L. J. Am. Chem. Soc. 1998, 120, 4039-4040
73. 2 yielded <5% of the amination product.
74. For some representative examples, see: Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337-339
75. Xi, Z.; Liu, F.; Zhou, Y.; Chen, W. Tetrahedron 2008, 64, 4254-4259
76. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490-3491
77. de Lange, B.; Lambers-Verstappen, M. H.; Schmieder-van de Vondervoort, L.; Sereinig, N.; de Rijk, R.; de Vries, A. H. M.; de Vries, J. G. Synlett 2006, 3105-3109
78. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742-8743
79. Andrus, M. B.; Chen, X. Tetrahedron 1997, 53, 16229-16240
80. These oxidants could readily be synthesized in gram quantities in a single step, commencing from commercially available reagents. See Supporting Information for further details.
81. 1H NMR analysis of the unpurified reaction mixture.
82. Br3Cu(NCMe) catalyst with PhI - NTs; see ref 4k. In contrast, a Rh-catalyst/sulfonimidamide system observed amination exclusively at the secondary carbon; see ref 4e.
83. For a discussion of C?H bond reactivity and steric effects in Rh-nitrene aminations, see ref 4j. With Cu-nitrene aminations, see refs 4e, 4h, 4k.
84. 3 C-H bonds; see: Li, Z.; Capretto, D. A.; Rahaman, R. O.; He, C. J. Am. Chem. Soc. 2007, 129, 12058-12059
85. For leading reviews and references on the Kharasch?Sosnovsky reaction, see: Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845-866
86. Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567-3571
87. Kharasch, M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80, 756
88. Powell, D. A.; Pelletier, G. Tetrahedron Lett. 2008, 49, 2495-2498
89. Borduas, N.; Powell, D. A. J. Org. Chem. 2008, 73, 7822-7825
90. 1H NMR spectrum of the unpurified reaction mixture.
91. Alternatively, carbon?nitrogen bond formation may proceed from an Cu(III) species. Aminations that proceed via aryl-Cu(III)-N species have recently been described, and Cu(III) intermediates have been proposed in other Cu-catalyzed allylic aminations; see refs 5a, 5c, and Huffman, L. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196-9197
92. For recent examples of aminations which proceed via postulated carbocations, see: Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409-413
93. Sreedhar, B.; Reddy, P. S.; Reddy, M. A.; Neelima, B.; Arundhathi, R. Tetrahedron Lett. 2007, 48, 8174-8177